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_7228476
_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, C3 H6 O, 0.25(C8 H12 O4)'
_chemical_formula_sum            'C41 H45 Br4 O10'
_chemical_formula_weight         1017.41
_space_group_crystal_system      orthorhombic
_space_group_IT_number           59
_space_group_name_Hall           '-P 2ab 2a'
_space_group_name_H-M_alt        'P m m n'
_symmetry_space_group_name_Hall  '-P 2ab 2a'
_symmetry_space_group_name_H-M   'P m m n :2'
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   16.2181(9)
_cell_length_b                   16.1822(8)
_cell_length_c                   7.9215(4)
_cell_measurement_reflns_used    3516
_cell_measurement_temperature    123.00(10)
_cell_measurement_theta_max      75.8570
_cell_measurement_theta_min      3.8400
_cell_volume                     2078.95(19)
_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      123.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1977
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
  1 omega  -57.00   32.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8676   57.0000    0.0000 89

  2 omega -116.00  -10.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8676  -77.0000 -120.0000 106

  3 omega   24.00   95.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       40.8676 -125.0000   90.0000 71

  4 omega  -31.00   69.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       40.8676  -57.0000   90.0000 100

  5 omega   41.00   94.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000   90.0000 53

  6 omega   36.00   91.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000  -60.0000 55

  7 omega   43.00   75.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -126.0000  -41.0000 32

  8 omega   86.00  175.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000 -150.0000 89

  9 omega   49.00  114.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000  120.0000 65

 10 omega   38.00   91.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000   30.0000 53

 11 omega   31.00  164.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -15.0000 -180.0000 133

 12 omega   39.00   98.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000 -180.0000 59

 13 omega   36.00   58.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000  -60.0000 22
;
_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      -0.0945187000
_diffrn_orient_matrix_UB_12      0.0006706000
_diffrn_orient_matrix_UB_13      0.0180418000
_diffrn_orient_matrix_UB_21      0.0056794000
_diffrn_orient_matrix_UB_22      -0.0672065000
_diffrn_orient_matrix_UB_23      0.1371111000
_diffrn_orient_matrix_UB_31      0.0065283000
_diffrn_orient_matrix_UB_32      0.0674594000
_diffrn_orient_matrix_UB_33      0.1368834000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0646
_diffrn_reflns_av_unetI/netI     0.0488
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            9568
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        66.742
_diffrn_reflns_theta_max         66.742
_diffrn_reflns_theta_min         5.585
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    5.191
_exptl_absorpt_correction_T_max  0.941
_exptl_absorpt_correction_T_min  0.803
_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    1.625
_exptl_crystal_description       needle
_exptl_crystal_F_000             1022
_exptl_crystal_size_max          0.1601
_exptl_crystal_size_mid          0.0413
_exptl_crystal_size_min          0.0259
_refine_diff_density_max         0.657
_refine_diff_density_min         -0.669
_refine_diff_density_rms         0.114
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     153
_refine_ls_number_reflns         1981
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0408
_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^)+(0.0610P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1006
_refine_ls_wR_factor_ref         0.1057
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1706
_reflns_number_total             1981
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ce00975e2.cif
_cod_data_source_block           acetone_BrC2
_cod_original_cell_volume        2078.96(19)
_cod_database_code               7228476
_chemical_oxdiff_formula         'C20 H20 N1 O9 Br4'
_reflns_odcompleteness_completeness 99.54
_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 O(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C12) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
3. Others
 Fixed Sof: H15A(0.5) H15B(0.5) H15C(0.5) C12(0.25) H12C(0.25) H12A(0.25)
 H12B(0.25)
4.a Riding coordinates:
 O1(H1)
4.b Ternary CH refined with riding coordinates:
 C5(H5)
4.c Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
4.d Aromatic/amide H refined with riding coordinates:
 C1(H1A), C6(H6)
4.e Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C15(H15A,H15B,H15C), C12(H12C,H12A,H12B)
;
_shelx_res_checksum              4422
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'