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_1553215
_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 ad
_chemical_formula_moiety         'C16 H17 Cl2 N O4'
_chemical_formula_sum            'C16 H17 Cl2 N O4'
_chemical_formula_weight         358.20
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-11-13
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.3061(2)
_cell_length_b                   9.7010(2)
_cell_length_c                   20.7173(6)
_cell_measurement_reflns_used    4443
_cell_measurement_temperature    294.39(10)
_cell_measurement_theta_max      72.4770
_cell_measurement_theta_min      4.2650
_cell_volume                     1669.35(7)
_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      294.39(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.001
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
  1 omega    1.00   75.00   1.0000    5.6250
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -99.0000  -30.0000 74

  2 omega   20.00  104.00   1.0000    5.6250
omega____ theta____ kappa____ phi______ frames
    -       36.5421   57.0000   60.0000 84

  3 omega    1.00   75.00   1.0000    5.6250
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -99.0000   60.0000 74

  4 omega  -31.00   53.00   1.0000    5.6250
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -57.0000   60.0000 84

  5 omega   10.00  104.00   1.0000    5.6250
omega____ theta____ kappa____ phi______ frames
    -       36.5421   77.0000  -90.0000 94

  6 omega   91.00  176.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -150.0000 85

  7 omega   38.00   91.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   30.0000 53

  8 omega   39.00  109.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -120.0000 70

  9 omega   39.00  109.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  120.0000 70

 10 omega   38.00   91.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  120.0000 53

 11 omega  100.00  178.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000   90.0000 78

 12 omega   81.00  176.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   30.0000 95

 13 omega  -31.00   53.00   1.0000    5.6250
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -57.0000  150.0000 84

 14 omega   20.00  104.00   1.0000    5.6250
omega____ theta____ kappa____ phi______ frames
    -       36.5421   57.0000  120.0000 84

 15 omega   20.00  104.00   1.0000    5.6250
omega____ theta____ kappa____ phi______ frames
    -       36.5421   57.0000    0.0000 84

 16 omega   20.00  104.00   1.0000    5.6250
omega____ theta____ kappa____ phi______ frames
    -       36.5421   57.0000 -180.0000 84
;
_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      0.1707009000
_diffrn_orient_matrix_UB_12      -0.0079404000
_diffrn_orient_matrix_UB_13      0.0287654000
_diffrn_orient_matrix_UB_21      0.0675487000
_diffrn_orient_matrix_UB_22      -0.0395697000
_diffrn_orient_matrix_UB_23      -0.0667104000
_diffrn_orient_matrix_UB_31      0.0263177000
_diffrn_orient_matrix_UB_32      0.1536637000
_diffrn_orient_matrix_UB_33      -0.0157450000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_Laue_measured_fraction_full 1.001
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            8970
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.075
_diffrn_reflns_theta_max         67.074
_diffrn_reflns_theta_min         4.268
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.671
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55989
_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    1.425
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.368
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details
;
 Flack x determined using 1055 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.004(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2975
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0510
_refine_ls_R_factor_gt           0.0478
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1284
_refine_ls_wR_factor_ref         0.1329
_reflns_Friedel_coverage         0.721
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                2749
_reflns_number_total             2975
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5qo00373c2.cif
_cod_data_source_block           lb-slq-7044
_cod_database_code               1553215
_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:
 C00E(H00A,H00D), C00H(H00E,H00F), C00I(H00H,H00I), C00L(H00J,H00L)
2.c Aromatic/amide H refined with riding coordinates:
 N004(H004), C00C(H00C), C00G(H00G), C00K(H00K), C00M(H00M)
2.d Idealised Me refined as rotating group:
 C00N(H00N,H00O,H00P)
;
_shelx_res_checksum              50067
_shelx_hkl_checksum              15778
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2015-11-12
_olex2_submission_special_instructions 'No special instructions were received'