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_7228481
_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, C13 H14 N2 O2, 4(C H4 O), C3 H6 O, H2 O'
_chemical_formula_sum            'C56 H74 Br4 N2 O16'
_chemical_formula_weight         1350.81
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_Hall           '-P 2yc'
_space_group_name_H-M_alt        'P 1 2/c 1'
_symmetry_space_group_name_Hall  '-P 2yc'
_symmetry_space_group_name_H-M   'P 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2017-04-07
_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                 91.3906(9)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   14.85237(16)
_cell_length_b                   7.94141(8)
_cell_length_c                   24.9573(2)
_cell_measurement_reflns_used    10685
_cell_measurement_temperature    123
_cell_measurement_theta_max      73.1160
_cell_measurement_theta_min      4.5580
_cell_volume                     2942.82(5)
_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_environment      air
_diffrn_ambient_temperature      123
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1977
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega  -70.00   30.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.3676   57.0000  -30.0000 100

  2 omega  -74.00   26.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.3676   77.0000   90.0000 100

  3 omega -108.00  -19.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.3676  -57.0000 -180.0000 89

  4 omega   30.00   91.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154  -30.0000  -60.0000 61

  5 omega   80.00  171.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154   30.0000 -150.0000 91

  6 omega   96.00  178.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154  125.0000   30.0000 82

  7 omega   78.00  176.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154   30.0000  120.0000 98

  8 omega   36.00  122.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154 -125.0000  -90.0000 86

  9 omega   23.00  109.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154  -94.0000  -30.0000 86

 10 omega   29.00   61.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154  -30.0000   90.0000 32

 11 omega   29.00  138.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154  -77.0000   60.0000 109
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0440278000
_diffrn_orient_matrix_UB_12      0.0863457000
_diffrn_orient_matrix_UB_13      -0.0480384000
_diffrn_orient_matrix_UB_21      -0.0748439000
_diffrn_orient_matrix_UB_22      -0.0699160000
_diffrn_orient_matrix_UB_23      -0.0375965000
_diffrn_orient_matrix_UB_31      -0.0567677000
_diffrn_orient_matrix_UB_32      0.1590448000
_diffrn_orient_matrix_UB_33      0.0095735000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            15504
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        66.740
_diffrn_reflns_theta_max         66.740
_diffrn_reflns_theta_min         2.976
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.907
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92714
_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.
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    1.524
_exptl_crystal_description       block
_exptl_crystal_F_000             1384
_exptl_crystal_size_max          0.1912
_exptl_crystal_size_mid          0.133
_exptl_crystal_size_min          0.1185
_refine_diff_density_max         0.658
_refine_diff_density_min         -0.690
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     436
_refine_ls_number_reflns         5219
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0288
_refine_ls_R_factor_gt           0.0269
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0316P)^2^+2.7779P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0664
_refine_ls_wR_factor_ref         0.0679
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4901
_reflns_number_total             5219
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ce00975e2.cif
_cod_data_source_block           acetone_BrC2_11
_cod_original_cell_volume        2942.81(5)
_cod_database_code               7228481
_chemical_oxdiff_formula         'C20 H20 N6 O10'
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, H4 of O4, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, H6A of O6, H3 of O3, H1 of O1, All O(H,H) groups
2. Others
 Fixed Sof: H27A(0.5) H27B(0.5) O9(0.5) H9D(0.5) H9E(0.5)
 Fixed U11: O9(0.14268)
 Fixed U33: O9(0.06501)
3.a Riding coordinates:
 O2(H2), O4(H4), O6(H6A), O5(H5)
3.b Free rotating group:
 O9(H9D,H9E)
3.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C19(H19A,H19B,H19C), C28(H28A,H28B,H28C)
;
_shelx_res_checksum              50257
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'