Endo-/Exo- and Halogen Bonded Complexes of Conformationally Rigid Cethyl-2-bromoresorcinarene and aromatic N-oxides
Puttreddy, Rakesh; Beyeh, Ngong Kodiah; Ras, Robin H.A.; Trant, John; Rissanen, Kari; CrystEngComm  (2017) –; doi:10.1039/C7CE00975E

data_7228483
_publ_section_title
;
 Endo-/Exo- and Halogen Bonded Complexes of Conformationally Rigid
 Cethyl-2-bromoresorcinarene and aromatic N-oxides
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/C7CE00975E
_journal_year                    2017
_chemical_formula_moiety         'C36 H36 Br4 O8, 3(C3 H6 O), 2(C6 H7 N O2)'
_chemical_formula_sum            'C57 H68 Br4 N2 O15'
_chemical_formula_weight         1340.77
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2017-04-21
_audit_creation_method
;
Olex2 1.2
(compiled 2016.08.25 svn.r3337 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2017-05-22 deposited with the CCDC.
2017-06-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.653(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   31.3059(19)
_cell_length_b                   8.0079(5)
_cell_length_c                   23.0375(17)
_cell_measurement_reflns_used    2463
_cell_measurement_temperature    120
_cell_measurement_theta_max      26.1420
_cell_measurement_theta_min      3.3660
_cell_volume                     5736.5(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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      120
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0053
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega  -78.00  -36.00   1.0000  125.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.1368 -178.0000 -180.0000 42

  2 omega  -83.00   -3.00   1.0000  125.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.1368  -57.0000 -180.0000 80

  3 omega  -35.00   -3.00   1.0000  125.0000
omega____ theta____ kappa____ phi______ frames
    -       19.3087  -57.0000   90.0000 32

  4 omega  -19.00    8.00   1.0000  125.0000
omega____ theta____ kappa____ phi______ frames
    -       19.3087  -99.0000 -180.0000 27

  5 omega   46.00   94.00   1.0000  125.0000
omega____ theta____ kappa____ phi______ frames
    -       19.3087  178.0000 -120.0000 48

  6 omega  -16.00   59.00   1.0000  125.0000
omega____ theta____ kappa____ phi______ frames
    -       19.3087  -99.0000    0.0000 75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0192179000
_diffrn_orient_matrix_UB_12      0.0083790000
_diffrn_orient_matrix_UB_13      0.0133044000
_diffrn_orient_matrix_UB_21      -0.0102596500
_diffrn_orient_matrix_UB_22      -0.0588995500
_diffrn_orient_matrix_UB_23      -0.0199599000
_diffrn_orient_matrix_UB_31      0.0067768500
_diffrn_orient_matrix_UB_32      -0.0656104500
_diffrn_orient_matrix_UB_33      0.0196299000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0650
_diffrn_reflns_av_unetI/netI     0.0911
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            14479
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.250
_diffrn_reflns_theta_max         25.250
_diffrn_reflns_theta_min         2.798
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.875
_exptl_absorpt_correction_T_max  0.921
_exptl_absorpt_correction_T_min  0.679
_exptl_absorpt_correction_type   gaussian
_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)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
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    1.552
_exptl_crystal_description       needle
_exptl_crystal_F_000             2736
_exptl_crystal_size_max          0.1695
_exptl_crystal_size_mid          0.0442
_exptl_crystal_size_min          0.0231
_refine_diff_density_max         1.681
_refine_diff_density_min         -0.944
_refine_diff_density_rms         0.180
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.146
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     354
_refine_ls_number_reflns         5192
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.146
_refine_ls_R_factor_all          0.1101
_refine_ls_R_factor_gt           0.0818
_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^)+(0.0488P)^2^+229.6943P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2002
_refine_ls_wR_factor_ref         0.2131
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3895
_reflns_number_total             5192
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ce00975e2.cif
_cod_data_source_block           acetone_BrC2_5
_cod_database_code               7228483
_chemical_oxdiff_formula         'C20 H20 O8 Br1'
_reflns_odcompleteness_completeness 99.76
_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, All O(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C14) = Uanis(C15)
3.a Riding coordinates:
 O1(H1), O2(H2), O4(H4)
3.b Ternary CH refined with riding coordinates:
 C3(H3A), C10(H10)
3.c Secondary CH2 refined with riding coordinates:
 C1AA(H1AA,H1AB), C11(H11A,H11B)
3.d Aromatic/amide H refined with riding coordinates:
 C9(H9), C13(H13), C17(H17), C18(H18), C20(H20), C21(H21)
3.e Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C32(H32A,H32B,H32C), C23(H23A,H23B,H23C), C22(H22A,H22B,
 H22C), C25(H25A,H25B,H25C), C27(H27A,H27B,H27C)
3.f Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_shelx_res_checksum              32876
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'