# Electronic Supplementary Material (ESI) for Materials Chemistry Frontiers.
# This journal is © the Partner Organisations 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_haoke5molt
_database_code_depnum_ccdc_archive 'CCDC 1481602'
_audit_update_record             
;
2016-05-24 deposited with the CCDC.	2019-04-17 downloaded from the CCDC.
;
_audit_creation_date             2016-04-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        d-DPE
_chemical_formula_moiety         'C20 H24'
_chemical_formula_sum            'C20 H24'
_chemical_formula_weight         264.39
_chemical_melting_point          ?
_chemical_oxdiff_formula         'ph2 Me6 C2 H2'
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'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.7535(5)
_cell_length_b                   6.1267(13)
_cell_length_c                   13.209(2)
_cell_angle_alpha                96.215(15)
_cell_angle_beta                 96.738(11)
_cell_angle_gamma                91.369(13)
_cell_volume                     379.54(11)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    926
_cell_measurement_temperature    100.01(1)
_cell_measurement_theta_max      28.9870
_cell_measurement_theta_min      4.3230
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.065
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86527
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.157
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             144
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_av_unetI/netI     0.0622
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            2089
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_min         3.532
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      100.01(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3587
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.943
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega    6.00   82.30   0.7000   35.0000
omega____ theta____ kappa____ phi______ frames
    -       15.8574   57.0000 -120.0000 109

#__ type_ start__ end____ width___ exp.time_
  2 omega  -43.00   48.00   0.7000   35.0000
omega____ theta____ kappa____ phi______ frames
    -       15.8574  -57.0000  -30.0000 130

#__ type_ start__ end____ width___ exp.time_
  3 omega  -57.00   47.30   0.7000   35.0000
omega____ theta____ kappa____ phi______ frames
    -       15.8574  -57.0000   90.0000 149
;
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Mo at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0738826000
_diffrn_orient_matrix_UB_12      -0.0507969000
_diffrn_orient_matrix_UB_13      -0.0467002000
_diffrn_orient_matrix_UB_21      0.0004439000
_diffrn_orient_matrix_UB_22      -0.1022504000
_diffrn_orient_matrix_UB_23      0.0205744000
_diffrn_orient_matrix_UB_31      -0.1309511000
_diffrn_orient_matrix_UB_32      0.0233541000
_diffrn_orient_matrix_UB_33      0.0188798000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_source_current           0.80
_diffrn_source_power             0.040
_diffrn_source_target            Mo
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                978
_reflns_number_total             1410
_reflns_odcompleteness_completeness 98.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.04
_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, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     94
_refine_ls_number_reflns         1410
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0868
_refine_ls_R_factor_gt           0.0581
_refine_ls_restrained_S_all      1.002
_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)+(0.0680P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1305
_refine_ls_wR_factor_ref         0.1498
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C10(H10)
2.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
C1 C 0.4957(3) 0.1129(3) 0.36856(13) 0.0161(4) Uani 1 1 d . . . . .
C2 C 0.3945(3) 0.3032(3) 0.32745(13) 0.0167(4) Uani 1 1 d . . . . .
C3 C 0.4786(3) 0.3495(3) 0.23395(13) 0.0170(4) Uani 1 1 d . . . . .
H3 H 0.4146 0.4796 0.2069 0.020 Uiso 1 1 calc R . . . .
C4 C 0.6511(3) 0.2151(3) 0.17856(13) 0.0179(4) Uani 1 1 d . . . . .
C5 C 0.7468(3) 0.0222(3) 0.21863(13) 0.0162(4) Uani 1 1 d . . . . .
C6 C 0.6662(3) -0.0238(3) 0.31190(13) 0.0171(4) Uani 1 1 d . . . . .
H6 H 0.7298 -0.1543 0.3386 0.020 Uiso 1 1 calc R . . . .
C7 C 0.2038(3) 0.4556(3) 0.38224(13) 0.0198(5) Uani 1 1 d . . . . .
H7A H 0.1877 0.5915 0.3494 0.030 Uiso 1 1 calc GR . . . .
H7B H 0.2840 0.4901 0.4542 0.030 Uiso 1 1 calc GR . . . .
H7C H 0.0155 0.3845 0.3788 0.030 Uiso 1 1 calc GR . . . .
C8 C 0.7360(3) 0.2738(3) 0.07889(13) 0.0226(5) Uani 1 1 d . . . . .
H8A H 0.6504 0.4119 0.0629 0.034 Uiso 1 1 calc GR . . . .
H8B H 0.6701 0.1567 0.0241 0.034 Uiso 1 1 calc GR . . . .
H8C H 0.9429 0.2913 0.0845 0.034 Uiso 1 1 calc GR . . . .
C9 C 0.9321(3) -0.1297(3) 0.16188(13) 0.0211(5) Uani 1 1 d . . . . .
H9A H 1.1169 -0.0562 0.1608 0.032 Uiso 1 1 calc GR . . . .
H9B H 0.8425 -0.1694 0.0914 0.032 Uiso 1 1 calc GR . . . .
H9C H 0.9581 -0.2629 0.1964 0.032 Uiso 1 1 calc GR . . . .
C10 C 0.4226(3) 0.0586(3) 0.46826(13) 0.0175(4) Uani 1 1 d . . . . .
H10 H 0.2499 0.1118 0.4892 0.021 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
C1 C2 1.410(2) . ?
C1 C6 1.399(2) . ?
C1 C10 1.471(2) . ?
C2 C3 1.397(2) . ?
C2 C7 1.505(2) . ?
C3 C4 1.389(2) . ?
C4 C5 1.410(2) . ?
C4 C8 1.499(2) . ?
C5 C6 1.387(2) . ?
C5 C9 1.499(2) . ?
C10 C10 1.331(3) 2_656 ?

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
C2 C1 C10 120.86(15) . . ?
C6 C1 C2 118.37(16) . . ?
C6 C1 C10 120.77(16) . . ?
C1 C2 C7 121.68(16) . . ?
C3 C2 C1 118.16(15) . . ?
C3 C2 C7 120.16(16) . . ?
C4 C3 C2 123.30(16) . . ?
C3 C4 C5 118.47(16) . . ?
C3 C4 C8 120.96(16) . . ?
C5 C4 C8 120.57(16) . . ?
C4 C5 C9 120.78(16) . . ?
C6 C5 C4 118.52(16) . . ?
C6 C5 C9 120.70(16) . . ?
C5 C6 C1 123.14(16) . . ?
C10 C10 C1 125.63(18) 2_656 . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2016-04-12
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Vapour deposition'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_haoke7cult
_database_code_depnum_ccdc_archive 'CCDC 1564140'
_audit_update_record             
;
2017-07-22 deposited with the CCDC.	2019-04-17 downloaded from the CCDC.
;
_audit_creation_date             2017-05-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C24 H26'
_chemical_formula_sum            'C24 H26'
_chemical_formula_weight         314.45
_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'

_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/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   12.9394(12)
_cell_length_b                   8.2851(7)
_cell_length_c                   9.0830(8)
_cell_angle_alpha                90
_cell_angle_beta                 106.480(10)
_cell_angle_gamma                90
_cell_volume                     933.74(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1310
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.4090
_cell_measurement_theta_min      6.4160
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.466
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85950
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (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_primary    colourless
_exptl_crystal_density_diffrn    1.118
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.03
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0390
_diffrn_reflns_av_unetI/netI     0.0500
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            2713
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         67.475
_diffrn_reflns_theta_min         3.562
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3577
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    128.00 161.00   1.00    2.00    --  110.57 111.00  60.00   33
  2  ω   -108.00 -13.00   1.00    1.00    --  -40.45 -57.00 -90.00   95
  3  ω   -117.00 -21.00   1.00    1.00    --  -40.45 -37.00 150.00   96
  4  ω    109.00 177.00   1.00    2.00    --  110.57 111.00 150.00   68
  5  ω     89.00 149.00   1.00    2.00    --  110.57  61.00 -30.00   60
  6  ω     95.00 178.00   1.00    2.00    --  110.57  45.00 -90.00   83
  7  ω     53.00  83.00   1.00    1.00    --   40.45-125.00 -30.00   30
  8  ω     36.00 141.00   1.00    2.00    --  110.57 -61.00 120.00  105
;
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0049035000
_diffrn_orient_matrix_UB_12      -0.1165918000
_diffrn_orient_matrix_UB_13      0.1309700000
_diffrn_orient_matrix_UB_21      -0.1233701000
_diffrn_orient_matrix_UB_22      0.0209432000
_diffrn_orient_matrix_UB_23      -0.0429711000
_diffrn_orient_matrix_UB_31      -0.0134161000
_diffrn_orient_matrix_UB_32      -0.1433238000
_diffrn_orient_matrix_UB_33      -0.1104561000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           0.80
_diffrn_source_power             0.040
_diffrn_source_target            Cu
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1358
_reflns_number_total             1643
_reflns_odcompleteness_completeness 98.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     112
_refine_ls_number_reflns         1643
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0556
_refine_ls_R_factor_gt           0.0468
_refine_ls_restrained_S_all      1.001
_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)+(0.0640P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1216
_refine_ls_wR_factor_ref         0.1301
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C11(H11), C12(H12)
2.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
C1 C 0.19784(12) 0.37369(19) 0.45287(16) 0.0224(4) Uani 1 1 d . . . . .
C2 C 0.21881(12) 0.2084(2) 0.46445(16) 0.0236(4) Uani 1 1 d . . . . .
C3 C 0.31002(12) 0.1491(2) 0.42891(16) 0.0260(4) Uani 1 1 d . . . . .
H3 H 0.3246 0.0366 0.4377 0.031 Uiso 1 1 calc R . . . .
C4 C 0.38005(12) 0.2501(2) 0.38109(16) 0.0272(4) Uani 1 1 d . . . . .
C5 C 0.35985(12) 0.4135(2) 0.37504(17) 0.0288(4) Uani 1 1 d . . . . .
H5 H 0.4086 0.4843 0.3463 0.035 Uiso 1 1 calc R . . . .
C6 C 0.27016(12) 0.4782(2) 0.40970(16) 0.0260(4) Uani 1 1 d . . . . .
C7 C 0.14448(13) 0.0947(2) 0.51464(18) 0.0300(4) Uani 1 1 d . . . . .
H7A H 0.0751 0.0898 0.4352 0.045 Uiso 1 1 calc GR . . . .
H7B H 0.1333 0.1336 0.6109 0.045 Uiso 1 1 calc GR . . . .
H7C H 0.1767 -0.0132 0.5305 0.045 Uiso 1 1 calc GR . . . .
C8 C 0.47285(14) 0.1819(3) 0.3309(2) 0.0379(5) Uani 1 1 d . . . . .
H8A H 0.4500 0.1646 0.2196 0.057 Uiso 1 1 calc GR . . . .
H8B H 0.4955 0.0789 0.3831 0.057 Uiso 1 1 calc GR . . . .
H8C H 0.5333 0.2580 0.3573 0.057 Uiso 1 1 calc GR . . . .
C9 C 0.24899(14) 0.6566(2) 0.3946(2) 0.0379(4) Uani 1 1 d . . . . .
H9A H 0.3021 0.7079 0.3514 0.057 Uiso 1 1 calc GR . . . .
H9B H 0.2547 0.7025 0.4960 0.057 Uiso 1 1 calc GR . . . .
H9C H 0.1764 0.6756 0.3265 0.057 Uiso 1 1 calc GR . . . .
C10 C 0.09651(12) 0.43888(19) 0.47859(16) 0.0226(3) Uani 1 1 d . . . . .
C11 C 0.09760(12) 0.5261(2) 0.60985(17) 0.0270(4) Uani 1 1 d . . . . .
H11 H 0.1640 0.5449 0.6858 0.032 Uiso 1 1 calc R . . . .
C12 C 0.00261(12) 0.5861(2) 0.63114(17) 0.0271(4) Uani 1 1 d . . . . .
H12 H 0.0050 0.6451 0.7218 0.033 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
C1 C2 1.394(2) . ?
C1 C6 1.410(2) . ?
C1 C10 1.496(2) . ?
C2 C3 1.398(2) . ?
C2 C7 1.506(2) . ?
C3 C4 1.390(2) . ?
C4 C5 1.377(2) . ?
C4 C8 1.510(2) . ?
C5 C6 1.393(2) . ?
C6 C9 1.502(2) . ?
C10 C11 1.391(2) . ?
C10 C12 1.399(2) 3_566 ?
C11 C12 1.389(2) . ?
C12 C10 1.399(2) 3_566 ?

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
C2 C1 C6 119.59(14) . . ?
C2 C1 C10 120.21(13) . . ?
C6 C1 C10 120.12(14) . . ?
C1 C2 C3 119.13(14) . . ?
C1 C2 C7 120.65(13) . . ?
C3 C2 C7 120.22(14) . . ?
C4 C3 C2 121.89(15) . . ?
C3 C4 C8 120.94(16) . . ?
C5 C4 C3 118.10(14) . . ?
C5 C4 C8 120.92(15) . . ?
C4 C5 C6 122.01(15) . . ?
C1 C6 C9 120.75(14) . . ?
C5 C6 C1 119.20(15) . . ?
C5 C6 C9 120.00(14) . . ?
C11 C10 C1 121.68(13) . . ?
C11 C10 C12 118.16(14) . 3_566 ?
C12 C10 C1 120.16(13) 3_566 . ?
C12 C11 C10 120.73(14) . . ?
C11 C12 C10 121.11(14) . 3_566 ?

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
C1 C2 C3 C4 -0.5(2) . . . . ?
C1 C10 C11 C12 179.76(14) . . . . ?
C2 C1 C6 C5 1.8(2) . . . . ?
C2 C1 C6 C9 179.32(14) . . . . ?
C2 C1 C10 C11 107.99(18) . . . . ?
C2 C1 C10 C12 -72.49(19) . . . 3_566 ?
C2 C3 C4 C5 2.5(2) . . . . ?
C2 C3 C4 C8 -174.92(14) . . . . ?
C3 C4 C5 C6 -2.4(2) . . . . ?
C4 C5 C6 C1 0.2(2) . . . . ?
C4 C5 C6 C9 -177.27(15) . . . . ?
C6 C1 C2 C3 -1.7(2) . . . . ?
C6 C1 C2 C7 178.28(13) . . . . ?
C6 C1 C10 C11 -75.00(19) . . . . ?
C6 C1 C10 C12 104.52(18) . . . 3_566 ?
C7 C2 C3 C4 179.51(13) . . . . ?
C8 C4 C5 C6 175.08(14) . . . . ?
C10 C1 C2 C3 175.34(12) . . . . ?
C10 C1 C2 C7 -4.7(2) . . . . ?
C10 C1 C6 C5 -175.18(13) . . . . ?
C10 C1 C6 C9 2.3(2) . . . . ?
C10 C11 C12 C10 -0.2(3) . . . 3_566 ?
C12 C10 C11 C12 0.2(3) 3_566 . . . ?

_olex2_date_sample_data_collection 2017-05-05
_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 1.258
_oxdiff_exptl_absorpt_empirical_full_min 0.855
####################################################################### 
# 
# 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_161208_tph_tm
_database_code_depnum_ccdc_archive 'CCDC 1522067'
_audit_update_record             
;
2016-12-12 deposited with the CCDC.	2019-04-17 downloaded from the CCDC.
;
_audit_creation_date             2016-12-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_chemical_name_common            ?
_chemical_name_systematic        TPh-TM
_chemical_formula_moiety         'C24 H26'
_chemical_formula_sum            'C24 H26'
_chemical_formula_weight         314.45
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c10 h10 n2 o8'
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'

_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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.9294(8)
_cell_length_b                   7.3834(7)
_cell_length_c                   16.2178(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.745(8)
_cell_angle_gamma                90.00
_cell_volume                     949.41(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1377
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.4536
_cell_measurement_theta_min      2.8392
_exptl_absorpt_coefficient_mu    0.062
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91472
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.100
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.3
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_av_unetI/netI     0.0332
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            3766
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         2.84
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0196795000
_diffrn_orient_matrix_UB_12      -0.0102437000
_diffrn_orient_matrix_UB_13      -0.0422434000
_diffrn_orient_matrix_UB_21      -0.0869369000
_diffrn_orient_matrix_UB_22      0.0066656000
_diffrn_orient_matrix_UB_23      -0.0105657000
_diffrn_orient_matrix_UB_31      0.0081379000
_diffrn_orient_matrix_UB_32      0.0953003000
_diffrn_orient_matrix_UB_33      -0.0038048000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1283
_reflns_number_total             1729
_reflns_odcompleteness_completeness 99.48
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     112
_refine_ls_number_reflns         1729
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0686
_refine_ls_R_factor_gt           0.0497
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0656P)²+0.1720P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1315
_refine_ls_wR_factor_ref         0.1493
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C8(H8), C9(H9)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
C1 C 0.3955(2) 0.1889(2) 0.18190(10) 0.0432(4) Uani 1 d . . .
C2 C 0.4080(2) 0.1197(2) 0.26136(11) 0.0494(5) Uani 1 d . . .
H2 H 0.3465 0.0164 0.2741 0.059 Uiso 1 calc . . R
C3 C 0.5077(2) 0.1974(3) 0.32254(11) 0.0501(5) Uani 1 d . . .
C4 C 0.5969(2) 0.3539(3) 0.30467(10) 0.0481(5) Uani 1 d . . .
C5 C 0.5864(2) 0.4228(2) 0.22529(10) 0.0447(5) Uani 1 d . . .
H5 H 0.6467 0.5273 0.2130 0.054 Uiso 1 calc . . R
C6 C 0.4898(2) 0.3425(2) 0.16314(9) 0.0384(4) Uani 1 d . . .
C7 C 0.4925(2) 0.4221(2) 0.07913(9) 0.0381(4) Uani 1 d . . .
C8 C 0.4453(2) 0.6002(2) 0.06535(10) 0.0458(5) Uani 1 d . . .
H8 H 0.4078 0.6700 0.1092 0.055 Uiso 1 calc . . R
C9 C 0.5472(2) 0.3243(2) 0.01199(10) 0.0468(5) Uani 1 d . . .
H9 H 0.5798 0.2043 0.0193 0.056 Uiso 1 calc . . R
C10 C 0.2791(3) 0.0997(3) 0.12015(12) 0.0651(6) Uani 1 d . . .
H10A H 0.3439 0.0277 0.0828 0.098 Uiso 1 calc . . GR
H10B H 0.2184 0.1910 0.0898 0.098 Uiso 1 calc . . GR
H10C H 0.2006 0.0236 0.1485 0.098 Uiso 1 calc . . GR
C11 C 0.5178(3) 0.1125(3) 0.40687(13) 0.0767(7) Uani 1 d . . .
H11A H 0.4710 0.1940 0.4467 0.115 Uiso 1 calc . . GR
H11B H 0.6335 0.0882 0.4210 0.115 Uiso 1 calc . . GR
H11C H 0.4552 0.0012 0.4067 0.115 Uiso 1 calc . . GR
C12 C 0.7019(3) 0.4511(3) 0.36887(12) 0.0740(7) Uani 1 d . . .
H12A H 0.7595 0.5508 0.3437 0.111 Uiso 1 calc . . GR
H12B H 0.7831 0.3688 0.3923 0.111 Uiso 1 calc . . GR
H12C H 0.6300 0.4956 0.4115 0.111 Uiso 1 calc . . GR


_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
C1 C2 1.388(2) . ?
C1 C6 1.394(2) . ?
C1 C10 1.505(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.385(3) . ?
C3 C4 1.387(3) . ?
C3 C11 1.506(2) . ?
C4 C5 1.386(2) . ?
C4 C12 1.507(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.391(2) . ?
C6 C7 1.484(2) . ?
C7 C8 1.385(2) . ?
C7 C9 1.381(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.375(2) 3_665 ?
C9 C8 1.375(2) 3_665 ?
C9 H9 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 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
C2 C1 C6 118.03(16) . . ?
C2 C1 C10 119.50(16) . . ?
C6 C1 C10 122.46(15) . . ?
C1 C2 H2 118.5 . . ?
C3 C2 C1 123.07(17) . . ?
C3 C2 H2 118.5 . . ?
C2 C3 C4 118.89(15) . . ?
C2 C3 C11 120.08(18) . . ?
C4 C3 C11 121.03(18) . . ?
C3 C4 C12 122.07(16) . . ?
C5 C4 C3 118.38(16) . . ?
C5 C4 C12 119.55(18) . . ?
C4 C5 H5 118.6 . . ?
C4 C5 C6 122.85(16) . . ?
C6 C5 H5 118.6 . . ?
C1 C6 C7 122.48(15) . . ?
C5 C6 C1 118.72(15) . . ?
C5 C6 C7 118.80(15) . . ?
C8 C7 C6 121.13(14) . . ?
C9 C7 C6 121.68(14) . . ?
C9 C7 C8 117.15(14) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 C7 121.17(15) 3_665 . ?
C9 C8 H8 119.4 3_665 . ?
C7 C9 H9 119.2 . . ?
C8 C9 C7 121.68(15) 3_665 . ?
C8 C9 H9 119.2 3_665 . ?
C1 C10 H10A 109.5 . . ?
C1 C10 H10B 109.5 . . ?
C1 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C3 C11 H11A 109.5 . . ?
C3 C11 H11B 109.5 . . ?
C3 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C4 C12 H12A 109.5 . . ?
C4 C12 H12B 109.5 . . ?
C4 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 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
C1 C2 C3 C4 1.4(3) . . . . ?
C1 C2 C3 C11 -178.72(16) . . . . ?
C1 C6 C7 C8 122.26(19) . . . . ?
C1 C6 C7 C9 -59.9(2) . . . . ?
C2 C1 C6 C5 -2.4(2) . . . . ?
C2 C1 C6 C7 176.85(14) . . . . ?
C2 C3 C4 C5 -2.0(3) . . . . ?
C2 C3 C4 C12 177.23(18) . . . . ?
C3 C4 C5 C6 0.4(3) . . . . ?
C4 C5 C6 C1 1.8(3) . . . . ?
C4 C5 C6 C7 -177.41(14) . . . . ?
C5 C6 C7 C8 -58.5(2) . . . . ?
C5 C6 C7 C9 119.34(18) . . . . ?
C6 C1 C2 C3 0.8(3) . . . . ?
C6 C7 C8 C9 177.95(16) . . . 3_665 ?
C6 C7 C9 C8 -177.94(16) . . . 3_665 ?
C8 C7 C9 C8 0.0(3) . . . 3_665 ?
C9 C7 C8 C9 0.0(3) . . . 3_665 ?
C10 C1 C2 C3 -177.74(17) . . . . ?
C10 C1 C6 C5 176.13(17) . . . . ?
C10 C1 C6 C7 -4.7(3) . . . . ?
C11 C3 C4 C5 178.16(17) . . . . ?
C11 C3 C4 C12 -2.6(3) . . . . ?
C12 C4 C5 C6 -178.84(17) . . . . ?

_exptl_crystal_recrystallization_method 'Vapour deposition'
####################################################################### 
# 
# 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_170615_246_dpe_tm
_database_code_depnum_ccdc_archive 'CCDC 1585455'
loop_
_audit_author_name
_audit_author_address
'Haoke Zhang' 'Hong Kong University of Science and Technology'
_audit_update_record             
;
2017-11-14 deposited with the CCDC.	2019-04-17 downloaded from the CCDC.
;
_audit_creation_date             2017-06-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H24'
_chemical_formula_sum            'C20 H24'
_chemical_formula_weight         264.39
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c10 h10'
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'

_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                   4.8732(6)
_cell_length_b                   10.6116(13)
_cell_length_c                   15.5489(18)
_cell_angle_alpha                90
_cell_angle_beta                 90.251(10)
_cell_angle_gamma                90
_cell_volume                     804.07(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    946
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.2536
_cell_measurement_theta_min      3.8326
_shelx_estimated_absorpt_T_max   0.986
_shelx_estimated_absorpt_T_min   0.971
_exptl_absorpt_coefficient_mu    0.061
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54366
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.092
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.23
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_av_unetI/netI     0.0376
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4786
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.350
_diffrn_reflns_theta_min         3.840
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -52.00   34.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       11.7808  -38.0000  -90.0000 86

#__ type_ start__ end____ width___ exp.time_
  2 omega  -14.00   77.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       11.7808   77.0000 -180.0000 91

#__ type_ start__ end____ width___ exp.time_
  3 omega  -13.00   87.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       11.7808   38.0000   90.0000 100
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0430619000
_diffrn_orient_matrix_UB_12      0.0637976000
_diffrn_orient_matrix_UB_13      0.0014811000
_diffrn_orient_matrix_UB_21      0.0284148000
_diffrn_orient_matrix_UB_22      -0.0018911000
_diffrn_orient_matrix_UB_23      -0.0446965000
_diffrn_orient_matrix_UB_31      -0.1361289000
_diffrn_orient_matrix_UB_32      0.0197562000
_diffrn_orient_matrix_UB_33      -0.0090587000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                935
_reflns_number_total             1460
_reflns_odcompleteness_completeness 99.66
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.425
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     94
_refine_ls_number_reflns         1460
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1057
_refine_ls_R_factor_gt           0.0722
_refine_ls_restrained_S_all      1.058
_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)+(0.1159P)²+0.2071P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1979
_refine_ls_wR_factor_ref         0.2347
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C7(H7)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
C1 C 0.8440(6) 0.2127(2) 1.01551(17) 0.0627(8) Uani 1 1 d . . . . .
C2 C 1.0352(5) 0.3029(2) 0.99083(19) 0.0646(8) Uani 1 1 d . . . . .
H2 H 1.114861 0.353485 1.032887 0.077 Uiso 1 1 calc R . . . .
C3 C 1.1108(5) 0.3200(2) 0.90630(19) 0.0629(8) Uani 1 1 d . . . . .
C4 C 0.9877(5) 0.2429(3) 0.84555(18) 0.0628(8) Uani 1 1 d . . . . .
H4 H 1.037055 0.252035 0.788173 0.075 Uiso 1 1 calc R . . . .
C5 C 0.7946(5) 0.1531(2) 0.86672(16) 0.0587(7) Uani 1 1 d . . . . .
C6 C 0.7203(5) 0.1372(2) 0.95281(16) 0.0571(7) Uani 1 1 d . . . . .
C7 C 0.4971(6) 0.0445(2) 0.97193(16) 0.0688(8) Uani 1 1 d . . . . .
H7 H 0.336692 0.052137 0.939711 0.083 Uiso 1 1 calc R . . . .
C8 C 0.7698(8) 0.2033(3) 1.1092(2) 0.0945(12) Uani 1 1 d . . . . .
H8A H 0.574891 0.192913 1.114542 0.142 Uiso 1 1 calc GR . . . .
H8B H 0.825533 0.278888 1.138374 0.142 Uiso 1 1 calc GR . . . .
H8C H 0.861502 0.132200 1.134416 0.142 Uiso 1 1 calc GR . . . .
C9 C 1.3187(6) 0.4173(3) 0.8816(2) 0.0838(10) Uani 1 1 d . . . . .
H9A H 1.499880 0.384900 0.891747 0.126 Uiso 1 1 calc GR . . . .
H9B H 1.291775 0.491871 0.915577 0.126 Uiso 1 1 calc GR . . . .
H9C H 1.297659 0.437659 0.821815 0.126 Uiso 1 1 calc GR . . . .
C10 C 0.6670(6) 0.0739(3) 0.79642(18) 0.0805(10) Uani 1 1 d . . . . .
H10A H 0.473970 0.091327 0.793019 0.121 Uiso 1 1 calc GR . . . .
H10B H 0.694546 -0.013697 0.809092 0.121 Uiso 1 1 calc GR . . . .
H10C H 0.751505 0.093923 0.742447 0.121 Uiso 1 1 calc GR . . . .


_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
C1 C2 1.391(4) . ?
C1 C6 1.396(4) . ?
C1 C8 1.506(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.379(4) . ?
C3 C4 1.384(4) . ?
C3 C9 1.498(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.381(4) . ?
C5 C6 1.398(3) . ?
C5 C10 1.510(4) . ?
C6 C7 1.498(4) . ?
C7 C7 1.287(5) 3_657 ?
C7 H7 0.9300 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 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
C2 C1 C6 119.3(2) . . ?
C2 C1 C8 118.5(3) . . ?
C6 C1 C8 122.2(2) . . ?
C1 C2 H2 118.8 . . ?
C3 C2 C1 122.4(3) . . ?
C3 C2 H2 118.8 . . ?
C2 C3 C4 117.1(2) . . ?
C2 C3 C9 121.3(3) . . ?
C4 C3 C9 121.6(3) . . ?
C3 C4 H4 118.7 . . ?
C5 C4 C3 122.6(3) . . ?
C5 C4 H4 118.7 . . ?
C4 C5 C6 119.4(2) . . ?
C4 C5 C10 119.4(2) . . ?
C6 C5 C10 121.2(2) . . ?
C1 C6 C5 119.1(2) . . ?
C1 C6 C7 123.4(2) . . ?
C5 C6 C7 117.4(2) . . ?
C6 C7 H7 116.4 . . ?
C7 C7 C6 127.1(4) 3_657 . ?
C7 C7 H7 116.4 3_657 . ?
C1 C8 H8A 109.5 . . ?
C1 C8 H8B 109.5 . . ?
C1 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C3 C9 H9A 109.5 . . ?
C3 C9 H9B 109.5 . . ?
C3 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C5 C10 H10A 109.5 . . ?
C5 C10 H10B 109.5 . . ?
C5 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
