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_7228477
_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, 2(C6 H7 N O), C3 H6 O'
_chemical_formula_sum            'C51 H56 Br4 N2 O11'
_chemical_formula_weight         1192.61
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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                90.848(2)
_cell_angle_beta                 115.869(4)
_cell_angle_gamma                90.012(3)
_cell_formula_units_Z            2
_cell_length_a                   13.8485(6)
_cell_length_b                   13.9210(4)
_cell_length_c                   14.3337(4)
_cell_measurement_reflns_used    9561
_cell_measurement_temperature    120.00(10)
_cell_measurement_theta_max      73.2450
_cell_measurement_theta_min      3.3870
_cell_volume                     2486.08(17)
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1977
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details
;
  1 omega  -45.00  -19.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.3676   37.0000  -60.0000 26

  2 omega   -8.00   25.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.3676   37.0000  -60.0000 33

  3 omega  -44.00   26.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.3676   37.0000 -180.0000 70

  4 omega  -95.00  -13.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.3676  125.0000 -120.0000 82

  5 omega   61.00   98.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154  -45.0000  120.0000 37

  6 omega   32.00  109.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154  -94.0000   90.0000 77

  7 omega   40.00   89.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154  -30.0000  -90.0000 49

  8 omega   89.00  147.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154   45.0000 -180.0000 58

  9 omega   85.00  163.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154   77.0000 -150.0000 78

 10 omega  104.00  175.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154  125.0000  150.0000 71

 11 omega  -47.00    5.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.6176   37.0000  120.0000 52

 12 omega  -45.00   24.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.6176   37.0000   60.0000 69

 13 omega   33.00   83.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154  -45.0000   90.0000 50

 14 omega   26.00  107.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154  -94.0000  -30.0000 81

 15 omega   36.00   62.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154 -125.0000 -120.0000 26

 16 omega   71.00  118.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154 -125.0000 -120.0000 47

 17 omega   95.00  177.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154  125.0000   30.0000 82

 18 omega   80.00  146.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154   77.0000   90.0000 66

 19 omega   13.00   99.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       41.6176   57.0000  150.0000 86
;
_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      -0.0048314000
_diffrn_orient_matrix_UB_12      -0.0906534000
_diffrn_orient_matrix_UB_13      -0.0648989000
_diffrn_orient_matrix_UB_21      0.1144811000
_diffrn_orient_matrix_UB_22      0.0213226000
_diffrn_orient_matrix_UB_23      0.0132289000
_diffrn_orient_matrix_UB_31      0.0464409000
_diffrn_orient_matrix_UB_32      -0.0598101000
_diffrn_orient_matrix_UB_33      0.0994228000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_av_unetI/netI     0.0476
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16207
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        66.749
_diffrn_reflns_theta_max         66.749
_diffrn_reflns_theta_min         3.427
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.466
_exptl_absorpt_correction_T_max  0.744
_exptl_absorpt_correction_T_min  0.547
_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_density_diffrn    1.593
_exptl_crystal_F_000             1208
_exptl_crystal_size_max          0.1148
_exptl_crystal_size_mid          0.0906
_exptl_crystal_size_min          0.0545
_refine_diff_density_max         0.802
_refine_diff_density_min         -0.568
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     641
_refine_ls_number_reflns         8742
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0381
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0326P)^2^+3.1574P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0931
_refine_ls_wR_factor_ref         0.0966
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7754
_reflns_number_total             8742
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ce00975e2.cif
_cod_data_source_block           2_BrC2
_cod_original_cell_volume        2486.07(17)
_cod_database_code               7228477
_chemical_oxdiff_formula         'C5 H5 N1 O3 Br1'
_reflns_odcompleteness_completeness 99.13
_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
2. Restrained distances
 O7-H7
 0.85 with sigma of 0.02
 H5-O5
 0.85 with sigma of 0.02
 H3-O3
 0.85 with sigma of 0.02
 O1-H1
 0.85 with sigma of 0.02
 O6-H6
 0.85 with sigma of 0.02
 O4-H4
 0.85 with sigma of 0.02
 H2-O2
 0.85 with sigma of 0.02
 H8-O8
 0.85 with sigma of 0.02
3.a Riding coordinates:
 O8(H8), O4(H4), O6(H6), O2(H2)
3.b Ternary CH refined with riding coordinates:
 C7(H7A), C25(H25), C34(H34), C16(H16)
3.c Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C8(H8A,H8B), C35(H35A,H35B), C26(H26A,H26B)
3.d Aromatic/amide H refined with riding coordinates:
 C15(H15), C33(H33), C24(H24), C42(H42), C46(H46), C40(H40), C49(H49), C6(H6A),
  C43(H43), C48(H48), C41(H41), C47(H47)
3.e Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C27(H27A,H27B,H27C), C18(H18A,H18B,H18C), C36(H36A,H36B,
 H36C), C39(H39A,H39B,H39C), C51(H51A,H51B,H51C), C37(H37A,H37B,H37C), C45(H45A,
 H45B,H45C)
;
_shelx_res_checksum              8959
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'