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_7228479
_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(C10 H8 N2 O2), 3(C3 H6 O)'
_chemical_formula_sum            'C75 H78 Br4 N6 O17'
_chemical_formula_weight         1655.07
_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             2017-05-09
_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                 120.42(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   37.615(8)
_cell_length_b                   7.8003(16)
_cell_length_c                   27.830(6)
_cell_measurement_reflns_used    10353
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      73.1380
_cell_measurement_theta_min      3.6550
_cell_volume                     7041(3)
_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      N~2~
_diffrn_ambient_temperature      120.01(10)
_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  -46.00   33.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.3676   37.0000  -90.0000 79

  2 omega  -49.00   -4.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.3676   37.0000 -120.0000 45

  3 omega  -96.00   -7.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.3676  125.0000  -30.0000 89

  4 omega -114.00  -25.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.3676  -37.0000   90.0000 89

  5 omega   33.00   91.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154  -30.0000  -60.0000 58

  6 omega   53.00  121.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154   15.0000  -60.0000 68

  7 omega   61.00  173.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154   15.0000 -180.0000 112

  8 omega   98.00  173.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154  125.0000 -150.0000 75

  9 omega   41.00   99.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154  -45.0000  120.0000 58

 10 omega   32.00  122.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154 -125.0000   90.0000 90

 11 omega   26.00  109.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154  -94.0000  150.0000 83

 12 omega   30.00   89.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154  -30.0000 -120.0000 59

 13 omega   31.00  136.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154  -73.0000 -122.0000 105
;
_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      0.0201194000
_diffrn_orient_matrix_UB_12      -0.1232074000
_diffrn_orient_matrix_UB_13      -0.0099238000
_diffrn_orient_matrix_UB_21      -0.0327794000
_diffrn_orient_matrix_UB_22      -0.1366391000
_diffrn_orient_matrix_UB_23      -0.0314106000
_diffrn_orient_matrix_UB_31      -0.0278506000
_diffrn_orient_matrix_UB_32      0.0718906000
_diffrn_orient_matrix_UB_33      -0.0766715000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       44
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            21198
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.249
_diffrn_reflns_theta_min         1.516
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.362
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85341
_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)
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    1.561
_exptl_crystal_description       needle
_exptl_crystal_F_000             3384
_exptl_crystal_size_max          0.1712
_exptl_crystal_size_mid          0.0805
_exptl_crystal_size_min          0.0549
_refine_diff_density_max         3.166
_refine_diff_density_min         -0.787
_refine_diff_density_rms         0.141
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     466
_refine_ls_number_reflns         6382
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0605
_refine_ls_R_factor_gt           0.0566
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0993P)^2^+33.2637P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1443
_refine_ls_wR_factor_ref         0.1499
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5827
_reflns_number_total             6382
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ce00975e2.cif
_cod_data_source_block           acetone_BrC2_10
_cod_original_cell_volume        7042(3)
_cod_database_code               7228479
_chemical_oxdiff_formula         'C10 H20 N4 O4 Br1'
_reflns_odcompleteness_completeness 99.88
_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
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Riding coordinates:
 O1(H1), O2(H2), O3(H3), O4(H4)
2.b Ternary CH refined with riding coordinates:
 C13(H13), C16(H16)
2.c Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C17(H17A,H17B)
2.d Aromatic/amide H refined with riding coordinates:
 C6(H6), C12(H12), C19(H19), C20(H20), C21(H21), C22(H22), C25(H25), C26(H26),
 C27(H27), C28(H28), C29(H29), C30(H30), C32(H32), C33(H33)
2.e Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C18(H18A,H18B,H18C), C35(H35A,H35B,H35C), C36(H36A,H36B,
 H36C), C38(H38A,H38B,H38C)
;
_shelx_res_checksum              45680
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'