A general synthesis of dendralenes
George, Josemon; Ward, Jas S.; Sherburn, Michael S.; Chemical Science 10 (2019) 9969–; doi:10.1039/C9SC03976G

data_1556931
_publ_section_title
;
 A general synthesis of dendralenes
;
_journal_issue                   43
_journal_name_full               'Chemical Science'
_journal_page_first              9969
_journal_paper_doi               10.1039/C9SC03976G
_journal_volume                  10
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C25 H24 N2 O4'
_chemical_formula_sum            'C25 H24 N2 O4'
_chemical_formula_weight         416.46
_space_group_crystal_system      tetragonal
_space_group_IT_number           82
_space_group_name_Hall           'I -4'
_space_group_name_H-M_alt        'I -4'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc22jzf1
_audit_creation_date             2019-05-22
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-06-14 deposited with the CCDC.	2019-09-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.1165(5)
_cell_length_b                   18.1165(5)
_cell_length_c                   12.8619(11)
_cell_measurement_reflns_used    2954
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.3340
_cell_measurement_theta_min      4.2010
_cell_volume                     4221.4(4)
_computing_cell_refinement       'CrysAlisPro 1.171.40.36a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.36a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.36a (Rigaku OD, 2018)'
_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      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.1297
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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 -72.00   1.00    3.00    --  -36.95 -57.00 150.00   31
  2  \w    -45.00 -20.00   1.00    3.00    --  -36.95 -46.00 -84.64   25
  3  \w     81.00 107.00   1.00    3.00    --   36.95  19.00-120.00   26
  4  \w     31.00  65.00   1.00    3.00    --   36.95  57.00  30.00   34
  5  \w      4.00  29.00   1.00    3.00    --   36.95  88.00  41.48   25
  6  \w      2.00  55.00   1.00    3.00    --   36.95 -38.00-150.00   53
  7  \w     32.00  57.00   1.00    3.00    --   36.95  19.00-120.00   25
  8  \w     14.00 103.00   1.00    3.00    --   36.95  19.00  60.00   89
  9  \w     26.00  51.00   1.00    3.00    --   36.95  38.00   0.00   25
 10  \w      6.00  53.00   1.00    3.00    --   36.95 -99.00 150.00   47
 11  \w     33.00  83.00   1.00    3.00    --   36.95-125.00 -60.00   50
 12  \w      5.00  30.00   1.00    3.00    --   36.95  89.00-101.73   25
 13  \w     83.00 110.00   1.00   12.00    --  111.00 -25.00-150.00   27
 14  \w    138.00 165.00   1.00   12.00    --  111.00  50.00 -60.00   27
 15  \w     95.00 120.00   1.00   12.00    --  111.00  50.00 -60.00   25
 16  \w    129.00 156.00   1.00   12.00    --  111.00  64.00 -60.00   27
 17  \w     43.00  72.00   1.00   12.00    --  111.00 -92.00 150.00   29
 18  \w     73.00 109.00   1.00   12.00    --  111.00-111.00   0.00   36
 19  \w     92.00 119.00   1.00   12.00    --  111.00  38.00  30.00   27
 20  \w     90.00 117.00   1.00   12.00    --  111.00  25.00   0.00   27
 21  \w    145.00 177.00   1.00   12.00    --  111.00  25.00   0.00   32
 22  \w     45.00  77.00   1.00   12.00    --  111.00 -25.00-150.00   32
 23  \w     94.00 120.00   1.00   12.00    --  111.00  50.00 -30.00   26
 24  \w     91.00 117.00   1.00   12.00    --  111.00  64.00 -30.00   26
 25  \w    101.00 177.00   1.00   12.00    --  111.00  38.00 150.00   76
 26  \w     88.00 120.00   1.00   12.00    --  111.00  25.00 -60.00   32
 27  \w     92.00 118.00   1.00   12.00    --  111.00  38.00 -30.00   26
 28  \w    141.00 168.00   1.00   12.00    --  111.00  64.00   0.00   27
 29  \w     91.00 117.00   1.00   12.00    --  111.00  64.00 -60.00   26
 30  \w     86.00 113.00   1.00   12.00    --  111.00 -77.00-120.00   27
 31  \w     42.00  67.00   1.00   12.00    --  111.00-111.00  60.00   25
 32  \w     45.00  85.00   1.00   12.00    --  111.00 -77.00-120.00   40
 33  \w     46.00 102.00   1.00   12.00    --  111.00 -25.00-120.00   56
 34  \w     88.00 115.00   1.00   12.00    --  111.00  25.00 -30.00   27
 35  \w     94.00 121.00   1.00   12.00    --  111.00  64.00   0.00   27
 36  \w     92.00 119.00   1.00   12.00    --  111.00  38.00 -60.00   27
 37  \w     95.00 120.00   1.00   12.00    --  111.00  50.00 -90.00   25
 38  \w     95.00 122.00   1.00   12.00    --  111.00  50.00  30.00   27
 39  \w    108.00 133.00   1.00   12.00    --  111.00 178.00 -60.00   25
 40  \w     91.00 118.00   1.00   12.00    --  111.00  64.00 -90.00   27
 41  \w    100.00 127.00   1.00   12.00    --  111.00  64.00  30.00   27
 42  \w     66.00  91.00   1.00   12.00    --  111.00 178.00 -60.00   25
 43  \w     94.00 119.00   1.00   12.00    --  111.00  38.00   0.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0088338000
_diffrn_orient_matrix_UB_12      0.0844777000
_diffrn_orient_matrix_UB_13      -0.0046358000
_diffrn_orient_matrix_UB_21      0.0845877000
_diffrn_orient_matrix_UB_22      -0.0087829000
_diffrn_orient_matrix_UB_23      0.0021793000
_diffrn_orient_matrix_UB_31      0.0011925000
_diffrn_orient_matrix_UB_32      -0.0033809000
_diffrn_orient_matrix_UB_33      -0.1196834000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0488
_diffrn_reflns_av_unetI/netI     0.0580
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12779
_diffrn_reflns_point_group_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        66.589
_diffrn_reflns_theta_max         66.589
_diffrn_reflns_theta_min         6.457
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.725
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83634
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.36a (Rigaku Oxford Diffraction, 2018)
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    1.311
_exptl_crystal_description       needle
_exptl_crystal_F_000             1760
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.037
_exptl_crystal_size_min          0.033
_refine_diff_density_max         0.134
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 1176 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.19(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         3605
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0405
_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^)+(0.0366P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0816
_refine_ls_wR_factor_ref         0.0871
_reflns_Friedel_coverage         0.845
_reflns_Friedel_fraction_full    0.932
_reflns_Friedel_fraction_max     0.932
_reflns_number_gt                3074
_reflns_number_total             3605
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc03976g3.cif
_cod_data_source_block           jg-g135-c1-f4-polarminorproductscaled
_cod_database_code               1556931
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         C25H24N2O4
_shelx_estimated_absorpt_t_max   0.976
_shelx_estimated_absorpt_t_min   0.817
_reflns_odcompleteness_completeness 98.36
_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.a Ternary CH refined with riding coordinates:
 C3(H3), C5(H5), C6(H6), C10(H10), C15(H15), C24(H24)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C19(H19), C20(H20), C21(H21), C22(H22), C23(H23)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C8(H8A,H8B,H8C), C13(H13A,H13B,H13C)
;
_shelx_res_checksum              1417
_shelx_fab_checksum              34755
_ins_header
;
TITL JG-G135-C1-F4-Polar minor productscaled in I4(1) 
REM I4(1) (#80 in standard setting)
CELL 1.54184  18.116510  18.116510  12.861925  90.0000  90.0000  90.0000
ZERR    8.00   0.000497   0.000497   0.001136   0.0000   0.0000   0.0000
LATT -2
SYMM -x+1/2,-y+1/2, z+1/2 
SYMM -y, x+1/2, z+1/4 
SYMM  y+1/2,-x, z+3/4 
SFAC C H N O
UNIT 200.00 192.00 16.00 32.00
TREF
HKLF 4
END
;
_olex2_date_sample_data_collection 2019-05-20
_olex2_date_sample_submission    2019-05-16
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder with oil'
_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 1.386
_oxdiff_exptl_absorpt_empirical_full_min 0.764