#------------------------------------------------------------------------------
#$Date: 2025-04-18 01:10:56 +0300 (Fri, 18 Apr 2025) $
#$Revision: 299319 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/44/1574418.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1574418
loop_
_publ_author_name
'Toyama, Yoshifumi'
'Nakamura, Takumu'
'Horikawa, Yushin'
'Morinaka, Yuta'
'Ono, Yohei'
'Yagi, Akiko'
'Itami, Kenichiro'
'Ito, Hideto'
_publ_section_title
;
 Rh-catalyzed mechanochemical transfer hydrogenation for the synthesis of
 periphery-hydrogenated polycyclic aromatic compounds
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D5SC01489A
_journal_year                    2025
_chemical_formula_moiety         'C42 H36'
_chemical_formula_sum            'C42 H36'
_chemical_formula_weight         540.7464
_chemical_name_systematic        7e
_space_group_crystal_system      orthorhombic
_space_group_IT_number           68
_space_group_name_Hall           '-C 2a 2ac'
_space_group_name_H-M_alt        'C c c a :2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2l6v0p
_audit_creation_date             2024-08-26
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2018.12.05 svn.r3537 for Rigaku Oxford Diffraction, GUI svn.r5625)
;
_audit_update_record
;
2024-10-10 deposited with the CCDC.	2025-04-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   25.7173(12)
_cell_length_b                   13.4757(6)
_cell_length_c                   8.5134(4)
_cell_measurement_reflns_used    4611
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      29.4650
_cell_measurement_theta_min      2.9210
_cell_volume                     2950.4(2)
_computing_cell_refinement       'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.868
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -6.00  26.00   0.50  120.00    --   -2.54 -87.00 115.00   64
  2  ω     14.00  46.00   0.50  120.00    --    3.16  57.00 -90.00   64
  3  ω    -13.00  69.00   0.50  120.00    --    3.16  57.00 -30.00  164
  4  ω      3.00  38.00   0.50  120.00    --    3.16 -99.00 -60.00   70
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0041695000
_diffrn_orient_matrix_UB_12      0.0221610000
_diffrn_orient_matrix_UB_13      -0.0745103000
_diffrn_orient_matrix_UB_21      0.0270610000
_diffrn_orient_matrix_UB_22      -0.0092238000
_diffrn_orient_matrix_UB_23      0.0069866000
_diffrn_orient_matrix_UB_31      -0.0033655000
_diffrn_orient_matrix_UB_32      -0.0468330000
_diffrn_orient_matrix_UB_33      -0.0366178000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_unetI/netI     0.0238
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.868
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            8767
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.868
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         29.557
_diffrn_reflns_theta_min         2.939
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65322
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.120a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_description       plate
_exptl_crystal_F_000             1152
_exptl_crystal_preparation       Luminescent
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: CHCl3/pentane'
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.350
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     96
_refine_ls_number_reflns         1797
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0387
_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)+(0.0578P)²+1.6299P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1035
_refine_ls_wR_factor_ref         0.1089
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1523
_reflns_number_total             1797
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5sc01489a2.cif
_cod_data_source_block
toy2011a_hydrogenated-ruburene_chcl3-pentane_xray_auto
_cod_original_sg_symbol_Hall     '-C 2b 2bc'
_cod_original_sg_symbol_H-M      'C c c e'
_cod_database_code               1574418
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H Cl'
_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.
;
_shelx_estimated_absorpt_t_max   0.999
_shelx_estimated_absorpt_t_min   0.993
_diffrn_oxdiff_digest_frames
;
0157a7e0762ce4822625fc3f3800e3b1ee000250ab9
;
_diffrn_oxdiff_digest_hkl
;
010905d7a748f4b8756d30f356e6c735c1f45b
;
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C4(H00A,H00B), C5(H00C,H00D)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H006), C11(H007), C10(H009), C8(H00E), C9(H00F)
;
_shelx_res_file
;
TITL toy2011a_hydrogenated-ruburene_chcl3-pentane_xray_auto_a.res in Ccca
    toy2011a_hydrogenated-ruburene_chcl3-pentane_xray_auto.res
    created by SHELXL-2018/3 at 10:12:24 on 26-Aug-2024
REM Old TITL toy2011a_hydrogenated-ruburene_chcl3-pentane_xray_auto_a.res in
REM Ccca
REM SHELXT solution in Ccca: R1 0.129, Rweak 0.002, Alpha 0.016
REM <I/s> 0.360 for 208 systematic absences, Orientation as input
REM Formula found by SHELXT: C21
CELL 0.71073 25.7173 13.4757 8.5134 90 90 90
ZERR 16 0.0012 0.0006 0.0004 0 0 0
LATT 7
SYMM 0.5-X,-Y,+Z
SYMM -X,+Y,0.5-Z
SYMM 0.5+X,-Y,0.5-Z
SFAC C H
UNIT 168 144

L.S. 20
PLAN  20
SIZE 0.02 0.1 0.1
TEMP -150(2)
list 4
fmap 2
acta 50
OMIT 2 0 0
REM <olex2.extras>
REM <HklSrc "%.\\TOY2011a_hydrogenated-ruburene_CHCl3-pentane_Xray_auto.hkl">
REM </olex2.extras>

WGHT    0.057800    1.629900
FVAR       0.30346
C2    1    0.445800    0.657229    0.272403    11.00000    0.01629    0.01426 =
         0.01566   -0.00035   -0.00010   -0.00138
C1    1    0.472172    0.750000    0.250000    10.50000    0.01564    0.01216 =
         0.01512   -0.00030    0.00000    0.00000
C3    1    0.472988    0.568471    0.268547    11.00000    0.01971    0.01225 =
         0.01572   -0.00052    0.00009   -0.00155
C6    1    0.389756    0.652905    0.320838    11.00000    0.01637    0.01287 =
         0.02349    0.00249    0.00074   -0.00124
C4    1    0.445308    0.471678    0.306991    11.00000    0.02489    0.01232 =
         0.02563    0.00046    0.00277   -0.00309
AFIX  23
H00A  2    0.426487    0.479603    0.407653    11.00000   -1.20000
H00B  2    0.419189    0.458137    0.224297    11.00000   -1.20000
AFIX   0
C7    1    0.376009    0.679965    0.473141    11.00000    0.02242    0.02302 =
         0.02451   -0.00012    0.00204    0.00001
AFIX  43
H006  2    0.401763    0.705243    0.542410    11.00000   -1.20000
AFIX   0
C11   1    0.351408    0.614582    0.222363    11.00000    0.02184    0.02374 =
         0.02603    0.00168   -0.00236   -0.00486
AFIX  43
H007  2    0.360196    0.594585    0.118702    11.00000   -1.20000
AFIX   0
C5    1    0.481546    0.383021    0.319837    11.00000    0.03287    0.01160 =
         0.02381    0.00144    0.00329   -0.00103
AFIX  23
H00C  2    0.461056    0.320832    0.321007    11.00000   -1.20000
H00D  2    0.501634    0.386896    0.418847    11.00000   -1.20000
AFIX   0
C10   1    0.300530    0.605378    0.274359    11.00000    0.02041    0.03943 =
         0.03992    0.00888   -0.00580   -0.00925
AFIX  43
H009  2    0.274694    0.579549    0.205882    11.00000   -1.20000
AFIX   0
C8    1    0.324879    0.670349    0.524964    11.00000    0.02878    0.04072 =
         0.03066    0.00309    0.01062    0.00317
AFIX  43
H00E  2    0.315921    0.689123    0.629064    11.00000   -1.20000
AFIX   0
C9    1    0.287179    0.633527    0.425079    11.00000    0.01842    0.04955 =
         0.04540    0.01300    0.00706   -0.00268
AFIX  43
H00F  2    0.252223    0.627593    0.459914    11.00000   -1.20000
AFIX   0
HKLF 4




REM  toy2011a_hydrogenated-ruburene_chcl3-pentane_xray_auto_a.res in Ccca
REM wR2 = 0.1089, GooF = S = 1.044, Restrained GooF = 1.044 for all data
REM R1 = 0.0387 for 1523 Fo > 4sig(Fo) and 0.0466 for all 1797 data
REM 96 parameters refined using 0 restraints

END

WGHT      0.0577      1.6345

REM Highest difference peak  0.350,  deepest hole -0.189,  1-sigma level  0.041
Q1    1   0.5000  0.5670  0.2500  10.50000  0.05    0.35
Q2    1   0.4187  0.6564  0.2930  11.00000  0.05    0.34
Q3    1   0.5000  0.7500  0.2500  10.25000  0.05    0.32
Q4    1   0.4608  0.6150  0.2911  11.00000  0.05    0.29
Q5    1   0.4600  0.5214  0.2785  11.00000  0.05    0.27
Q6    1   0.3696  0.6405  0.2697  11.00000  0.05    0.26
Q7    1   0.4583  0.7023  0.2570  11.00000  0.05    0.26
Q8    1   0.5000  0.3842  0.2500  10.50000  0.05    0.25
Q9    1   0.4626  0.4226  0.3060  11.00000  0.05    0.24
Q10   1   0.3268  0.6124  0.2542  11.00000  0.05    0.19
Q11   1   0.3491  0.6946  0.4837  11.00000  0.05    0.19
Q12   1   0.3505  0.6603  0.4974  11.00000  0.05    0.19
Q13   1   0.3780  0.6838  0.3811  11.00000  0.05    0.18
Q14   1   0.3014  0.6155  0.3551  11.00000  0.05    0.16
Q15   1   0.3873  0.6465  0.4075  11.00000  0.05    0.14
Q16   1   0.3066  0.6708  0.4548  11.00000  0.05    0.14
Q17   1   0.4105  0.4883  0.3390  11.00000  0.05    0.09
Q18   1   0.4081  0.4649  0.3062  11.00000  0.05    0.09
Q19   1   0.4615  0.3363  0.3654  11.00000  0.05    0.09
Q20   1   0.4293  0.8155  0.4726  11.00000  0.05    0.09
;
_shelx_res_checksum              49069
_olex2_exptl_crystal_mounting_method loop
_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 1.582
_oxdiff_exptl_absorpt_empirical_full_min 0.742
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z'
'-x, y, -z+1/2'
'x+1/2, -y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1, -y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'x+1, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z'
'x, -y, z-1/2'
'-x-1/2, y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x, y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
'-x, y+1/2, z-1/2'
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
C2 C 0.44580(4) 0.65723(6) 0.27240(11) 0.0154(2) Uani 1 1 d . . . . .
C1 C 0.47217(5) 0.750000 0.250000 0.0143(3) Uani 1 2 d S T P . .
C3 C 0.47299(3) 0.56847(7) 0.26855(11) 0.0159(2) Uani 1 1 d . . . . .
C6 C 0.38976(4) 0.65291(7) 0.32084(12) 0.0176(2) Uani 1 1 d . . . . .
C4 C 0.44531(4) 0.47168(7) 0.30699(12) 0.0209(2) Uani 1 1 d . . . . .
H00A H 0.426487 0.479603 0.407653 0.025 Uiso 1 1 calc R . . . .
H00B H 0.419189 0.458137 0.224297 0.025 Uiso 1 1 calc R . . . .
C7 C 0.37601(4) 0.67997(7) 0.47314(12) 0.0233(2) Uani 1 1 d . . . . .
H006 H 0.401763 0.705243 0.542410 0.028 Uiso 1 1 calc R . . . .
C11 C 0.35141(4) 0.61458(8) 0.22236(13) 0.0239(2) Uani 1 1 d . . . . .
H007 H 0.360196 0.594585 0.118702 0.029 Uiso 1 1 calc R . . . .
C5 C 0.48155(4) 0.38302(7) 0.31984(12) 0.0228(2) Uani 1 1 d . . . . .
H00C H 0.461056 0.320832 0.321007 0.027 Uiso 1 1 calc R . . . .
H00D H 0.501634 0.386896 0.418847 0.027 Uiso 1 1 calc R . . . .
C10 C 0.30053(4) 0.60538(10) 0.27436(15) 0.0333(3) Uani 1 1 d . . . . .
H009 H 0.274694 0.579549 0.205882 0.040 Uiso 1 1 calc R . . . .
C8 C 0.32488(5) 0.67035(10) 0.52496(14) 0.0334(3) Uani 1 1 d . . . . .
H00E H 0.315921 0.689123 0.629064 0.040 Uiso 1 1 calc R . . . .
C9 C 0.28718(4) 0.63353(10) 0.42508(16) 0.0378(3) Uani 1 1 d . . . . .
H00F H 0.252223 0.627593 0.459914 0.045 Uiso 1 1 calc R . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C2 0.0163(4) 0.0143(4) 0.0157(4) -0.0004(3) -0.0001(3) -0.0014(3)
C1 0.0156(6) 0.0122(6) 0.0151(6) -0.0003(4) 0.000 0.000
C3 0.0197(5) 0.0122(4) 0.0157(5) -0.0005(3) 0.0001(3) -0.0015(3)
C6 0.0164(4) 0.0129(4) 0.0235(5) 0.0025(3) 0.0007(3) -0.0012(3)
C4 0.0249(5) 0.0123(4) 0.0256(5) 0.0005(3) 0.0028(4) -0.0031(4)
C7 0.0224(5) 0.0230(5) 0.0245(5) -0.0001(4) 0.0020(4) 0.0000(4)
C11 0.0218(5) 0.0237(5) 0.0260(5) 0.0017(4) -0.0024(4) -0.0049(4)
C5 0.0329(5) 0.0116(4) 0.0238(5) 0.0014(3) 0.0033(4) -0.0010(4)
C10 0.0204(5) 0.0394(7) 0.0399(7) 0.0089(5) -0.0058(5) -0.0092(5)
C8 0.0288(6) 0.0407(7) 0.0307(6) 0.0031(5) 0.0106(5) 0.0032(5)
C9 0.0184(5) 0.0495(8) 0.0454(7) 0.0130(6) 0.0071(5) -0.0027(5)
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'
loop_
_citation_id
_citation_doi
_citation_year
1 10.26434/chemrxiv-2025-np2hv 2025
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 C2 C6 121.63(8) . . ?
C3 C2 C1 120.68(9) . . ?
C3 C2 C6 117.24(8) . . ?
C2 C1 C2 123.59(11) . 8_465 ?
C1 C1 C2 118.20(6) 6_565 8_465 ?
C1 C1 C2 118.20(6) 6_565 . ?
C2 C3 C3 119.82(5) . 3_655 ?
C2 C3 C4 119.92(8) . . ?
C3 C3 C4 120.26(5) 3_655 . ?
C7 C6 C2 119.32(9) . . ?
C7 C6 C11 118.52(9) . . ?
C11 C6 C2 121.93(9) . . ?
C5 C4 C3 113.74(8) . . ?
C6 C7 C8 120.68(10) . . ?
C10 C11 C6 120.58(10) . . ?
C4 C5 C5 109.05(7) . 3_655 ?
C9 C10 C11 120.43(11) . . ?
C9 C8 C7 120.05(11) . . ?
C10 C9 C8 119.73(11) . . ?
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
C2 C1 1.4350(10) . ?
C2 C3 1.3858(12) . ?
C2 C6 1.5003(13) . ?
C1 C1 1.431(2) 6_565 ?
C3 C3 1.4247(18) 3_655 ?
C3 C4 1.5216(12) . ?
C6 C7 1.3925(14) . ?
C6 C11 1.3936(14) . ?
C4 C5 1.5192(13) . ?
C7 C8 1.3930(15) . ?
C11 C10 1.3869(15) . ?
C5 C5 1.521(2) 3_655 ?
C10 C9 1.381(2) . ?
C8 C9 1.3818(18) . ?
