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

data_1556932
_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_formula_moiety         'C25 H24 N2 O4, H0.34 O0.17'
_chemical_formula_sum            'C25 H24.34 N2 O4.17'
_chemical_formula_weight         419.53
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc22jzh3
_audit_creation_date             2019-05-16
_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                 100.710(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   22.1402(8)
_cell_length_b                   6.8047(2)
_cell_length_c                   14.2360(5)
_cell_measurement_reflns_used    12495
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      29.5140
_cell_measurement_theta_min      4.1840
_cell_volume                     2107.40(13)
_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      150.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1872
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.908
_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    -44.00  42.00   1.00   47.50    --  -11.22  77.00 -60.00   86
  2  \w    -21.00  42.00   1.00   47.50    --   11.61  77.00 -60.00   63
  3  \w    -13.00  86.00   1.00   47.50    --   11.61  37.00-150.00   99
  4  \w    -42.00  44.00   1.00   47.50    --   11.61 -77.00  90.00   86
  5  \w    -15.00  53.00   1.00   47.50    --   11.61 -99.00-150.00   68
  6  \w    -44.00  14.00   1.00   47.50    --  -11.22  77.00  30.00   58
  7  \w    -21.00  42.00   1.00   47.50    --   11.61  77.00 120.00   63
  8  \w    -13.00  86.00   1.00   47.50    --   11.61  37.00  60.00   99
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Xcalibur, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0132119000
_diffrn_orient_matrix_UB_12      -0.0076759000
_diffrn_orient_matrix_UB_13      0.0492295000
_diffrn_orient_matrix_UB_21      -0.0290490000
_diffrn_orient_matrix_UB_22      -0.0264955000
_diffrn_orient_matrix_UB_23      0.0103402000
_diffrn_orient_matrix_UB_31      0.0066168000
_diffrn_orient_matrix_UB_32      -0.1005344000
_diffrn_orient_matrix_UB_33      -0.0064665000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_av_unetI/netI     0.0217
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.908
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            18911
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.860
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.931
_diffrn_reflns_theta_min         3.385
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94839
_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    1.322
_exptl_crystal_description       needle
_exptl_crystal_F_000             887
_exptl_crystal_size_max          0.664
_exptl_crystal_size_mid          0.285
_exptl_crystal_size_min          0.191
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 2015 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         5250
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0355
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0473P)^2^+0.6368P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0878
_refine_ls_wR_factor_ref         0.0904
_reflns_Friedel_coverage         0.758
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.805
_reflns_number_gt                4930
_reflns_number_total             5250
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc03976g3.cif
_cod_data_source_block           jg-g136scaled
_cod_database_code               1556932
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         C25H24N2O4
_reflns_odcompleteness_completeness 99.70
_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
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(O5)=FVAR(1)
 Sof(H5A)=2*FVAR(2)
3.a Ternary CH refined with riding coordinates:
 C3(H3), C7(H7), C16(H16), C20(H20), C24(H24)
3.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C21(H21A,H21B)
3.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15)
3.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C18(H18A,H18B,H18C), C23(H23A,H23B,H23C)
;
_shelx_res_checksum              27276
_ins_header
;
TITL JG-G136scaled in C2 
REM C2 (#5 in standard setting)
CELL 0.71073  22.140197   6.804719  14.236007  90.0000 100.7095  90.0000
ZERR    4.00   0.000847   0.000203   0.000540   0.0000   0.0036   0.0000
LATT -7
SYMM -x, y,-z 
SFAC C H N O
UNIT 100.00 96.00 8.00 16.00
TREF
HKLF 4
END
;
_olex2_date_sample_data_collection 2019-05-13
_olex2_date_sample_submission    2019-05-10
_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 1.071
_oxdiff_exptl_absorpt_empirical_full_min 0.932