A General Synthesis of Dendralenes
Sherburn, Michael; George, Josemon; Ward, Jas S.; Chemical Science  (2019) –; doi:10.1039/C9SC03976G

data_1552325
_publ_section_title
;
 A General Synthesis of Dendralenes
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/C9SC03976G
_journal_year                    2019
_chemical_formula_moiety         'C21 H20'
_chemical_formula_sum            'C21 H20'
_chemical_formula_weight         272.37
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-01-22
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2019-03-12 deposited with the CCDC.    2019-09-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.5470(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.59440(10)
_cell_length_b                   5.93120(10)
_cell_length_c                   16.3498(2)
_cell_measurement_reflns_used    6721
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      73.5890
_cell_measurement_theta_min      5.2920
_cell_volume                     806.71(2)
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.1297
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -54.00  30.00   1.00    1.00    --  -36.95  57.00 -60.00   84
  2  \w     10.00 105.00   1.00    1.00    --   36.95  77.00 -30.00   95
  3  \w     23.00  90.00   1.00    1.00    --   36.95-125.00-120.00   67
  4  \w    -34.00  66.00   1.00    1.00    --   36.95 -19.00   0.00  100
  5  \w     20.00 104.00   1.00    1.00    --   36.95  57.00-180.00   84
  6  \w    -31.00  64.00   1.00    1.00    --   36.95 -77.00  60.00   95
  7  \w      1.00  76.00   1.00    1.00    --   36.95 -99.00-120.00   75
  8  \w    -31.00  64.00   1.00    1.00    --   36.95 -77.00 -30.00   95
  9  \w     23.00  90.00   1.00    1.00    --   36.95-125.00 120.00   67
 10  \w     41.00 116.00   1.00    5.00    --  111.00-111.00 120.00   75
 11  \w     42.00 130.00   1.00    5.00    --  111.00 -38.00-180.00   88
 12  \w     44.00 131.00   1.00    5.00    --  111.00 -64.00-180.00   87
 13  \w     43.00 138.00   1.00    5.00    --  111.00 -77.00  60.00   95
 14  \w     91.00 178.00   1.00    5.00    --  111.00  64.00 -90.00   87
 15  \w     41.00 116.00   1.00    5.00    --  111.00-111.00-180.00   75
 16  \w     92.00 178.00   1.00    5.00    --  111.00  38.00  90.00   86
 17  \w     42.00 178.00   1.00    5.00    --  111.00   0.00-120.00  136
 18  \w     91.00 178.00   1.00    5.00    --  111.00  64.00-120.00   87
 19  \w     94.00 175.00   1.00    5.00    --  111.00  50.00 -90.00   81
 20  \w     82.00 128.00   1.00    5.00    --  111.00 -64.00 -60.00   46
 21  \w     65.00 136.00   1.00    5.00    --  111.00 -77.00 150.00   71
 22  \w     98.00 126.00   1.00    5.00    --  111.00 -64.00  30.00   28
 23  \w     82.00 114.00   1.00    5.00    --  111.00-111.00 -90.00   32
 24  \w     46.00  76.00   1.00    5.00    --  111.00 -64.00 -60.00   30
 25  \w     41.00  70.00   1.00    5.00    --  111.00-111.00  90.00   29
 26  \w     78.00 115.00   1.00    5.00    --  111.00-111.00  90.00   37
 27  \w     42.00  99.00   1.00    5.00    --  111.00 -12.00 -30.00   57
 28  \w     86.00 116.00   1.00    5.00    --  111.00-111.00  30.00   30
 29  \w     64.00 121.00   1.00    5.00    --  111.00 -92.00 -30.00   57
 30  \w     85.00 123.00   1.00    5.00    --  111.00 -38.00 -90.00   38
 31  \w     46.00  71.00   1.00    5.00    --  111.00 -38.00 -90.00   25
 32  \w    127.00 155.00   1.00    5.00    --  111.00 -12.00 -30.00   28
 33  \w     47.00  72.00   1.00    5.00    --  111.00-111.00 150.00   25
 34  \w    101.00 157.00   1.00    5.00    --  111.00 111.00 -30.00   56
 35  \w     61.00 102.00   1.00    5.00    --  111.00 -25.00 120.00   41
 36  \w    143.00 170.00   1.00    5.00    --  111.00  50.00 120.00   27
 37  \w     67.00  93.00   1.00    5.00    --  111.00 -64.00 -30.00   26
 38  \w     74.00 100.00   1.00    5.00    --  111.00 -42.00-132.08   26
 39  \w    102.00 127.00   1.00    5.00    --  111.00 -42.00-132.08   25
 40  \w     46.00  94.00   1.00    5.00    --  111.00 -38.00  90.00   48
 41  \w     82.00 108.00   1.00    5.00    --  111.00 -92.00  90.00   26
 42  \w     41.00  68.00   1.00    5.00    --  111.00-111.00 -90.00   27
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0484189000
_diffrn_orient_matrix_UB_12      0.2500651000
_diffrn_orient_matrix_UB_13      0.0002945000
_diffrn_orient_matrix_UB_21      -0.0460252000
_diffrn_orient_matrix_UB_22      -0.0357861000
_diffrn_orient_matrix_UB_23      0.0842846000
_diffrn_orient_matrix_UB_31      0.1726580000
_diffrn_orient_matrix_UB_32      0.0605602000
_diffrn_orient_matrix_UB_33      0.0487198000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0175
_diffrn_reflns_av_unetI/netI     0.0172
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            9802
_diffrn_reflns_point_group_measured_fraction_full 0.953
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         73.744
_diffrn_reflns_theta_min         5.317
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.471
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87143
_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_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.121
_exptl_crystal_description       needle
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.305
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.048
_refine_diff_density_max         0.404
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 1250 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3077
_refine_ls_number_restraints     13
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0457
_refine_ls_R_factor_gt           0.0451
_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/[\s^2^(Fo^2^)+(0.0621P)^2^+0.2761P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1264
_refine_ls_wR_factor_ref         0.1270
_reflns_Friedel_coverage         0.716
_reflns_Friedel_fraction_full    0.897
_reflns_Friedel_fraction_max     0.876
_reflns_number_gt                3018
_reflns_number_total             3077
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc03976g2.cif
_cod_data_source_block           JG-E139_scale
_cod_database_code               1552325
_shelxl_version_number           2014/6
_shelx_estimated_absorpt_t_max   0.978
_shelx_estimated_absorpt_t_min   0.870
_reflns_odcompleteness_completeness 98.47
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 C1A, C3A, C1B, C3B
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
3. Uiso/Uaniso restraints and constraints
C1A \\sim C3A \\sim C1B \\sim C3B: within 1.7A with sigma of 0.02 and sigma for
terminal atoms of 0.04
4. Others
 Sof(C1B)=Sof(H1BA)=Sof(H1BB)=Sof(H1BC)=Sof(C3B)=Sof(H3BA)=Sof(H3BB)=1-FVAR(1)
 Sof(C1A)=Sof(H1AA)=Sof(H1AB)=Sof(H1AC)=Sof(C3A)=Sof(H3AA)=Sof(H3AB)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21)
5.b X=CH2 refined with riding coordinates:
 C3A(H3AA,H3AB), C3B(H3BA,H3BB)
5.c Idealised Me refined as rotating group:
 C1A(H1AA,H1AB,H1AC), C1B(H1BA,H1BB,H1BC)
;
_shelx_res_checksum              89244
_ins_header
;
TITL JG-E139_scale in P2(1)/m 
REM P2(1)/m (#11 in standard setting)
CELL 1.54184   8.594375   5.931151  16.349805  90.0000 104.5472  90.0000
ZERR    2.00   0.000118   0.000074   0.000235   0.0000   0.0014   0.0000
LATT  1
SYMM -x, y+1/2,-z 
SFAC C H
UNIT 42.00 40.00
TREF
HKLF 4
END
;
_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 1.332
_oxdiff_exptl_absorpt_empirical_full_min 0.732