Synthesis and Study of 7,12,17-Trioxa[11]helicene.
Shyam Sundar, M.; Bedekar, Ashutosh V.; Organic letters 17 (2015) 5808–5811; doi:10.1021/acs.orglett.5b02948

data_1555434
_publ_section_title
;
 Synthesis and Study of 7,12,17-Trioxa[11]helicene.
;
_journal_issue                   23
_journal_name_full               'Organic letters'
_journal_page_first              5808
_journal_page_last               5811
_journal_paper_doi               10.1021/acs.orglett.5b02948
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C40 H20 O3'
_chemical_formula_sum            'C40 H20 O3'
_chemical_formula_weight         548.56
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_Int_Tables_number      14
_atom_sites_solution_primary     iterative
_audit_creation_date             2014-09-23
_audit_creation_method
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Olex2 1.2
(compiled 2014.06.27 svn.r2953 for OlexSys, GUI svn.r4874)
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_cell_angle_alpha                90
_cell_angle_beta                 99.906(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.63737(19)
_cell_length_b                   22.5914(7)
_cell_length_c                   15.1095(4)
_cell_measurement_reflns_used    5205
_cell_measurement_temperature    293
_cell_measurement_theta_max      75.2700
_cell_measurement_theta_min      3.5550
_cell_volume                     2568.11(12)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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_diffrn_ambient_temperature      293
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_diffrn_measured_fraction_theta_max 0.9979
_diffrn_measurement_details
;
  1 omega  -48.00   52.00   1.0000    6.6300
omega____ theta____ kappa____ phi______ frames
    -      -26.3214   38.0000    0.0000 100

  2 omega  -47.00   52.00   1.0000    6.6300
omega____ theta____ kappa____ phi______ frames
    -      -26.3214   38.0000  -90.0000 99

  3 omega   89.00  115.00   1.0000    6.6300
omega____ theta____ kappa____ phi______ frames
    -       26.3214  178.0000  -30.0000 26

  4 omega  -25.00    0.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      -72.5000   32.0000   30.0000 25

  5 omega  -46.00    7.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      -72.5000   32.0000 -150.0000 53

  6 omega  -66.00  -27.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      -72.5000   54.0000   60.0000 39

  7 omega  -87.00  -26.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      -72.5000  104.0000 -120.0000 61

  8 omega  -78.00  -43.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      -72.5000  104.0000  -60.0000 35

  9 omega  105.00  156.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -       75.1607  111.0000 -180.0000 51

 10 omega  119.00  152.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -       75.1607  124.0000  -55.0000 33

 11 omega  100.00  146.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -       75.1607  111.0000    0.0000 46

 12 omega   52.00  154.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -       75.1607   38.0000  120.0000 102

 13 omega  113.00  138.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -       75.1607  111.0000  -30.0000 25

 14 omega  151.00  177.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      124.0000  138.0000   90.0000 26

 15 omega   93.00  177.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      124.0000   54.0000   30.0000 84

 16 omega   43.00   68.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      124.0000  -32.0000  -90.0000 25

 17 omega  133.00  159.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      124.0000  104.0000  -30.0000 26

 18 omega  134.00  169.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      124.0000  104.0000    0.0000 35

 19 omega   46.00   98.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      124.0000 -104.0000 -150.0000 52

 20 omega   42.00   98.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      124.0000 -104.0000  -90.0000 56

 21 omega   63.00   89.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      124.0000  -32.0000   90.0000 26

 22 omega  141.00  167.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      124.0000  104.0000   30.0000 26

 23 omega   62.00  112.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      124.0000 -104.0000 -120.0000 50

 24 omega   66.00  108.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      124.0000  -54.0000  -90.0000 42

 25 omega   79.00  111.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      124.0000 -104.0000  -60.0000 32

 26 omega  152.00  178.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      124.0000  104.0000   60.0000 26

 27 omega   42.00   75.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      124.0000 -104.0000  -60.0000 33

 28 omega   42.00   99.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      124.0000  -21.0000 -150.0000 57

 29 omega  129.00  177.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      124.0000  -11.0000    0.0000 48

 30 omega   87.00  112.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      124.0000 -104.0000 -180.0000 25

 31 omega   42.00   97.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      124.0000  -11.0000    0.0000 55

 32 omega   87.00  112.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      124.0000 -104.0000   30.0000 25

 33 omega   91.00  136.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      124.0000   54.0000    0.0000 45

 34 omega   86.00  129.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      124.0000  138.0000  -30.0000 43

 35 omega   73.00   98.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      124.0000  -65.0000   90.0000 25

 36 omega  129.00  154.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      124.0000  -65.0000   90.0000 25

 37 omega   78.00  103.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      124.0000  -77.0000  150.0000 25

 38 omega   51.00   85.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      124.0000  -43.0000 -120.0000 34
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1318869000
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_diffrn_orient_matrix_UB_33      -0.0526605000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0203
_diffrn_reflns_av_unetI/netI     0.0261
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_diffrn_reflns_limit_h_min       -8
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_diffrn_reflns_limit_k_min       -28
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_diffrn_reflns_limit_l_min       -18
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_diffrn_reflns_theta_full        75.4748
_diffrn_reflns_theta_max         75.47
_diffrn_reflns_theta_min         3.56
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.704
_exptl_absorpt_correction_T_max  0.857
_exptl_absorpt_correction_T_min  0.815
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
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_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.4188
_exptl_crystal_description       plate
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_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.26
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_refine_diff_density_max         0.2227
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_refine_diff_density_rms         0.0386
_refine_ls_d_res_high            0.7964
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_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0523
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
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_refine_ls_number_parameters     396
_refine_ls_number_reflns         5323
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0523
_refine_ls_R_factor_all          0.0522
_refine_ls_R_factor_gt           0.0427
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0582P)^2^+0.2679P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1124
_refine_ls_wR_factor_ref         0.1209
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              28
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_reflns_limit_l_min              0
_reflns_number_gt                4385
_reflns_number_total             5333
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            ol5b02948_si_002.cif
_cod_data_source_block           exp_619
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1555434
_chemical_oxdiff_formula         'C H O'
_reflns_odcompleteness_completeness 94.04
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.95
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C24(H24), C26(H26), C27(H27), C28(H28), C29(H29), C31(H31), C32(H32),
 C33(H33), C34(H34), C35(H35), C36(H36), C37(H37), C38(H38), C39(H39), C40(H40),
  C41(H41), C42(H42), C43(H43)
;
_olex2_submission_special_instructions 'No special instructions were received'