Exploiting ortho-substitution effect on formation of oxygen-containing [10]paracyclophane through ring-closing metathesis
Yang, Li; Song, Liqiang; Huang, Chong; Huang, Mingzheng; Liu, Bo; Organic Chemistry Frontiers 3 (2016) 319–; doi:10.1039/C5QO00373C

data_1553216
_publ_section_title
;
 Exploiting ortho-substitution effect on formation of oxygen-containing
 [10]paracyclophane through ring-closing metathesis
;
_journal_issue                   3
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              319
_journal_paper_doi               10.1039/C5QO00373C
_journal_volume                  3
_journal_year                    2016
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C16 H17 Br2 N O4'
_chemical_formula_sum            'C16 H17 Br2 N O4'
_chemical_formula_weight         447.12
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-11-11
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2015-11-13 deposited with the CCDC.
2015-12-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.133(9)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.3327(7)
_cell_length_b                   9.5492(9)
_cell_length_c                   11.4501(10)
_cell_measurement_reflns_used    3461
_cell_measurement_temperature    292.36(10)
_cell_measurement_theta_max      72.1150
_cell_measurement_theta_min      4.5920
_cell_volume                     865.84(14)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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      292.36(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega   20.00  104.00   1.0000    4.4700
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000   30.0000 84

  2 omega  -31.00   53.00   1.0000    4.4700
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -57.0000  -60.0000 84

  3 omega    1.00   75.00   1.0000    4.4700
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -99.0000   30.0000 74

  4 omega   20.00  104.00   1.0000    4.4700
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000   90.0000 84

  5 omega  -33.00   55.00   1.0000    4.4700
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -38.0000   30.0000 88

  6 omega   17.00  105.00   1.0000    4.4700
omega____ theta____ kappa____ phi______ frames
    -       36.2921   38.0000  -30.0000 88

  7 omega  -31.00   53.00   1.0000    4.4700
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -57.0000  150.0000 84

  8 omega   10.00  104.00   1.0000    4.4700
omega____ theta____ kappa____ phi______ frames
    -       36.2921   77.0000  -30.0000 94

  9 omega   40.00   98.00   1.0000   17.8900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   30.0000 58

 10 omega   81.00  176.00   1.0000   17.8900
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -60.0000 95

 11 omega   90.00  175.00   1.0000   17.8900
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  -90.0000 85

 12 omega   91.00  176.00   1.0000   17.8900
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000   30.0000 85

 13 omega   38.00   91.00   1.0000   17.8900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -60.0000 53

 14 omega   70.00  178.00   1.0000   17.8900
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000  -30.0000 108

 15 omega   39.00  109.00   1.0000   17.8900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -30.0000 70

 16 omega   87.00  178.00   1.0000   17.8900
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  -30.0000 91

 17 omega   81.00  158.00   1.0000   17.8900
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   30.0000 77

 18 omega   90.00  116.00   1.0000   17.8900
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  -30.0000 26

 19 omega   82.00  109.00   1.0000   17.8900
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000    0.0000 27

 20 omega  129.00  175.00   1.0000   17.8900
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000    0.0000 46

 21 omega   88.00  121.00   1.0000   17.8900
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000   30.0000 33

 22 omega   88.00  113.00   1.0000   17.8900
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000   60.0000 25

 23 omega   91.00  116.00   1.0000   17.8900
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000   30.0000 25

 24 omega  147.00  173.00   1.0000   17.8900
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000   30.0000 26

 25 omega  128.00  175.00   1.0000   17.8900
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -30.0000 47

 26 omega   92.00  161.00   1.0000   17.8900
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000   60.0000 69

 27 omega   91.00  116.00   1.0000   17.8900
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  -60.0000 25

 28 omega   92.00  118.00   1.0000   17.8900
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -90.0000 26

 29 omega   82.00  109.00   1.0000   17.8900
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -30.0000 27

 30 omega   39.00  103.00   1.0000   17.8900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   60.0000 64

 31 omega   91.00  117.00   1.0000   17.8900
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000    0.0000 26

 32 omega   91.00  123.00   1.0000   17.8900
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000    0.0000 32

 33 omega   92.00  117.00   1.0000   17.8900
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000    0.0000 25

 34 omega   81.00  107.00   1.0000   17.8900
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -90.0000 26

 35 omega   43.00   69.00   1.0000   17.8900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   30.0000 26

 36 omega   71.00  105.00   1.0000   17.8900
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000    0.0000 34

 37 omega   89.00  114.00   1.0000   17.8900
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  -60.0000 25

 38 omega   71.00   97.00   1.0000   17.8900
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000   90.0000 26

 39 omega  116.00  178.00   1.0000   17.8900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -90.0000 62
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0059966000
_diffrn_orient_matrix_UB_12      0.0500985000
_diffrn_orient_matrix_UB_13      -0.1265145000
_diffrn_orient_matrix_UB_21      -0.1936187000
_diffrn_orient_matrix_UB_22      -0.0125533000
_diffrn_orient_matrix_UB_23      -0.0516754000
_diffrn_orient_matrix_UB_31      -0.0175945000
_diffrn_orient_matrix_UB_32      0.1528426000
_diffrn_orient_matrix_UB_33      0.0372010000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8597
_diffrn_reflns_point_group_measured_fraction_full 0.923
_diffrn_reflns_point_group_measured_fraction_max 0.923
_diffrn_reflns_theta_full        67.075
_diffrn_reflns_theta_max         67.075
_diffrn_reflns_theta_min         5.587
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    6.107
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53064
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.715
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.569
_refine_diff_density_min         -0.393
_refine_diff_density_rms         0.079
_refine_ls_abs_structure_details
;
 Flack x determined using 1028 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.06(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2858
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0459
_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^)+(0.0819P)^2^+0.1463P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1264
_refine_ls_wR_factor_ref         0.1290
_reflns_Friedel_coverage         0.734
_reflns_Friedel_fraction_full    0.836
_reflns_Friedel_fraction_max     0.836
_reflns_number_gt                2691
_reflns_number_total             2858
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5qo00373c2.cif
_cod_data_source_block           lliubo-slq-7043
_cod_original_cell_volume        865.83(14)
_cod_database_code               1553216
_reflns_odcompleteness_completeness 99.94
_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, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00B(H00B)
2.b Secondary CH2 refined with riding coordinates:
 C00C(H00c,H00d), C00D(H00e,H00f), C00E(H00g,H00h), C00M(H00k,H00l)
2.c Aromatic/amide H refined with riding coordinates:
 N006(H006), C009(H009), C00A(H00A), C00F(H00i), C00I(H00j)
2.d Idealised Me refined as rotating group:
 C00N(H00m,H00n,H00o)
;
_shelx_res_checksum              63439
_shelx_hkl_checksum              98541
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2015-11-09
_olex2_submission_special_instructions 'No special instructions were received'