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

data_1552323
_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 H18'
_chemical_formula_sum            'C21 H18'
_chemical_formula_weight         270.35
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-03-12
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-03-12 deposited with the CCDC.    2019-09-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.9002(3)
_cell_length_b                   20.0267(4)
_cell_length_c                   7.63560(10)
_cell_measurement_reflns_used    4184
_cell_measurement_temperature    293.80(17)
_cell_measurement_theta_max      70.6420
_cell_measurement_theta_min      4.0730
_cell_volume                     1666.81(6)
_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      air
_diffrn_ambient_temperature      293.80(17)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.1297
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.983
_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   -103.00 -19.00   1.00    1.00    --  -36.03 -57.00 -90.00   84
  2  \w    -33.00  55.00   1.00    1.00    --   36.03 -38.00  90.00   88
  3  \w     23.00  89.00   1.00    1.00    --   36.03-125.00 -90.00   66
  4  \w     91.00 176.00   1.00   11.07    --  108.91  61.00  30.00   85
  5  \w     82.00 176.00   1.00   11.07    --  108.91  77.00 120.00   94
  6  \w     39.00 110.00   1.00   11.07    --  108.91 -95.00 -90.00   71
  7  \w    100.00 178.00   1.00   11.07    --  108.91 111.00 150.00   78
  8  \w   -104.00  -9.00   1.00    1.00    --  -36.03 -77.00 150.00   95
  9  \w   -103.00 -19.00   1.00    1.00    --  -36.03 -57.00  30.00   84
 10  \w     71.00 178.00   1.00   11.07    --  108.91  15.00 -60.00  107
 11  \w     91.00 176.00   1.00   11.07    --  108.91  61.00-150.00   85
 12  \w     82.00 176.00   1.00   11.07    --  108.91  77.00 -30.00   94
 13  \w     42.00 127.00   1.00   11.07    --  108.91 -61.00  60.00   85
 14  \w    -31.00  39.00   1.00    1.00    --   36.03 -57.00   0.00   70
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0010217000
_diffrn_orient_matrix_UB_12      0.1991912000
_diffrn_orient_matrix_UB_13      -0.0121215000
_diffrn_orient_matrix_UB_21      0.0068427000
_diffrn_orient_matrix_UB_22      -0.0316786000
_diffrn_orient_matrix_UB_23      -0.0758787000
_diffrn_orient_matrix_UB_31      -0.1411966000
_diffrn_orient_matrix_UB_32      -0.0030223000
_diffrn_orient_matrix_UB_33      -0.0035791000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0138
_diffrn_reflns_av_unetI/netI     0.0151
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8784
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.717
_diffrn_reflns_theta_min         4.416
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.456
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67979
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.077
_exptl_crystal_description       plate
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.344
_exptl_crystal_size_min          0.166
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.132
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details
;
 Flack x determined using 1090 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   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3141
_refine_ls_number_restraints     19
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0579
_refine_ls_R_factor_gt           0.0505
_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^)+(0.0948P)^2^+0.1870P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1504
_refine_ls_wR_factor_ref         0.1605
_reflns_Friedel_coverage         0.777
_reflns_Friedel_fraction_full    0.933
_reflns_Friedel_fraction_max     0.894
_reflns_number_gt                2705
_reflns_number_total             3141
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc03976g2.cif
_cod_data_source_block           she18_05sn_scaled
_cod_database_code               1552323
_shelxl_version_number           2014/6
_shelx_estimated_absorpt_t_max   0.928
_shelx_estimated_absorpt_t_min   0.814
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 body (RIGU) restrains
 C19A, C19B, C20A, C20B, C21A, C21B
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
3. Others
 Sof(C19B)=Sof(C20B)=Sof(H20D)=Sof(H20E)=Sof(H20F)=Sof(C21B)=Sof(H21C)=
 Sof(H21D)=1-FVAR(1)
 Sof(C19A)=Sof(C20A)=Sof(H20A)=Sof(H20B)=Sof(H20C)=Sof(C21A)=Sof(H21A)=
 Sof(H21B)=FVAR(1)
4.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C8(H8), C10(H10), C14(H14),
 C15(H15), C16(H16), C17(H17), C18(H18)
4.b X=CH2 refined with riding coordinates:
 C21A(H21A,H21B), C21B(H21C,H21D)
4.c Idealised Me refined as rotating group:
 C20A(H20A,H20B,H20C), C20B(H20D,H20E,H20F)
;
_shelx_res_checksum              58913
_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 1.445
_oxdiff_exptl_absorpt_empirical_full_min 0.624