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_7228485
_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(C11 H9 N O), C3 H6 O'
_chemical_formula_sum            'C72 H69 Br4 N3 O12'
_chemical_formula_weight         1487.94
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_Hall           '-P 2yac'
_space_group_name_H-M_alt        'P 1 2/n 1'
_symmetry_space_group_name_Hall  '-P 2yac'
_symmetry_space_group_name_H-M   'P 1 2/n 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                 114.269(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   19.2354(5)
_cell_length_b                   7.84234(14)
_cell_length_c                   22.8722(6)
_cell_measurement_reflns_used    7405
_cell_measurement_temperature    123.00(10)
_cell_measurement_theta_max      73.1800
_cell_measurement_theta_min      3.8720
_cell_volume                     3145.37(15)
_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      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 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega -115.00  -19.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.3676  -37.0000   30.0000 96

  2 omega  -72.00   29.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.3676   77.0000 -150.0000 101

  3 omega   77.00  173.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154   61.0000  120.0000 96

  4 omega   82.00  175.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154   61.0000 -180.0000 93

  5 omega   50.00   94.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154  -45.0000 -180.0000 44

  6 omega   33.00  135.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154  -61.0000   30.0000 102

  7 omega   39.00   90.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154  -94.0000  -60.0000 51

  8 omega  -23.00   19.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.6176   37.0000  150.0000 42

  9 omega  -64.00   33.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.6176   77.0000  -30.0000 97

 10 omega  118.00  178.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154   45.0000   60.0000 60

 11 omega   85.00  111.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154   45.0000   30.0000 26

 12 omega   25.00   51.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154  -94.0000  120.0000 26

 13 omega   72.00  109.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154  -94.0000  120.0000 37

 14 omega   24.00  109.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154  -94.0000    0.0000 85

 15 omega  128.00  154.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154   45.0000   30.0000 26

 16 omega   34.00   76.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154 -125.0000  -90.0000 42
;
_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      0.0050365000
_diffrn_orient_matrix_UB_12      -0.0070742000
_diffrn_orient_matrix_UB_13      0.0689557000
_diffrn_orient_matrix_UB_21      -0.0386546000
_diffrn_orient_matrix_UB_22      0.1760782000
_diffrn_orient_matrix_UB_23      -0.0094667000
_diffrn_orient_matrix_UB_31      -0.0787209000
_diffrn_orient_matrix_UB_32      -0.0867675000
_diffrn_orient_matrix_UB_33      -0.0248337000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0611
_diffrn_reflns_av_unetI/netI     0.0598
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            17556
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        66.736
_diffrn_reflns_theta_max         66.736
_diffrn_reflns_theta_min         3.904
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.681
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89626
_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_density_diffrn    1.571
_exptl_crystal_F_000             1516
_exptl_crystal_size_max          0.0696
_exptl_crystal_size_mid          0.0559
_exptl_crystal_size_min          0.0277
_refine_diff_density_max         1.435
_refine_diff_density_min         -0.499
_refine_diff_density_rms         0.115
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     450
_refine_ls_number_reflns         5578
_refine_ls_number_restraints     41
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0451
_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^)+(0.0696P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1081
_refine_ls_wR_factor_ref         0.1147
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4769
_reflns_number_total             5578
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ce00975e2.cif
_cod_data_source_block           acetone_BrC2_7
_cod_original_cell_volume        3145.36(14)
_cod_database_code               7228485
_chemical_oxdiff_formula         'C20 H20 N1 O9'
_reflns_odcompleteness_completeness 99.87
_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. Restrained distances
 H4-O4
 0.85 with sigma of 0.02
 O7-N2
 1.34 with sigma of 0.02
 O3-H3
 0.85 with sigma of 0.02
 O2-H2
 0.85 with sigma of 0.02
 H5-O5
 0.85 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C32) \\sim Ueq, Uanis(C34) \\sim Ueq, Uanis(C31) \\sim Ueq, Uanis(C30)
\\sim Ueq, Uanis(N2) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms
of 0.02
Uanis(C37) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Fixed Sof: O7(0.5) C30(0.5) H30(0.5) C31(0.5) H31(0.5) C32(0.5) C33(0.5)
 H33(0.5) C34(0.5) H34(0.5) N2(0.5) C38(0.5) H38(0.5) C37(0.5) H37(0.5)
 C36(0.5) H36(0.5) C35(0.5) C40(0.5) H40(0.5) C39(0.5) H39(0.5)
 Fixed U11: O7(0.104627) C34(0.078601) C37(0.086901)
 Fixed U22: C37(0.0962)
 Fixed U33: C39(0.09185)
5.a Riding coordinates:
 O2(H2), O3(H3), O5(H5)
5.b Ternary CH refined with riding coordinates:
 C7(H7), C16(H16)
5.c Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C17(H17A,H17B)
5.d Aromatic/amide H refined with riding coordinates:
 C1(H1), C10(H10), C19(H19), C20(H20), C22(H22), C23(H23), C25(H25), C26(H26),
 C27(H27), C28(H28), C29(H29), C30(H30), C31(H31), C33(H33), C34(H34), C38(H38),
  C37(H37), C36(H36), C40(H40), C39(H39)
5.e Fitted hexagon refined as free rotating group:
 C30(C31,C32,C33,C34,N2), C38(C37,C36,C35,C40,C39)
5.f Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C18(H18A,H18B,H18C), C41(H41A,H41B,H41C)
;
_shelx_res_checksum              44983
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'