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_7228487
_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(C9 H7 N O), C3 H6 O'
_chemical_formula_sum            'C57 H56 Br4 N2 O11'
_chemical_formula_weight         1264.67
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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                 91.644(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.1188(3)
_cell_length_b                   26.2939(6)
_cell_length_c                   14.3240(3)
_cell_measurement_reflns_used    10437
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      75.1490
_cell_measurement_theta_min      4.2990
_cell_volume                     5315.4(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_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
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -65.00  31.00   1.00   10.00    --  -41.65  57.00-180.00   96
  2  \w   -110.00 -17.00   1.00   10.00    --  -41.65 -57.00  30.00   93
  3  \w    -66.00  33.00   1.00   10.00    --  -41.65  37.00 -30.00   99
  4  \w     43.00  98.00   1.00   10.00    --   41.65-125.00   0.00   55
  5  \w     29.00 109.00   1.00   42.50    --  112.00 -94.00 -90.00   80
  6  \w    100.00 178.00   1.00   42.50    --  112.00  61.00 120.00   78
  7  \w     79.00 177.00   1.00   42.50    --  112.00  77.00   0.00   98
  8  \w     45.00 138.00   1.00   42.50    --  112.00 -45.00  30.00   93
  9  \w     37.00 116.00   1.00   42.50    --  112.00-111.00-120.00   79
 10  \w     87.00 178.00   1.00   42.50    --  112.00  45.00  60.00   91
 11  \w     38.00 142.00   1.00   42.50    --  112.00 -77.00 -60.00  104
 12  \w     57.00 151.00   1.00   42.50    --  112.00 178.00 -90.00   94
 13  \w     65.00 116.00   1.00   42.50    --  112.00-111.00 120.00   51
 14  \w     89.00 178.00   1.00   42.50    --  112.00  61.00  90.00   89
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0950397000
_diffrn_orient_matrix_UB_12      0.0204655000
_diffrn_orient_matrix_UB_13      -0.0398795000
_diffrn_orient_matrix_UB_21      0.0142385000
_diffrn_orient_matrix_UB_22      0.0493600000
_diffrn_orient_matrix_UB_23      0.0566401000
_diffrn_orient_matrix_UB_31      0.0517803000
_diffrn_orient_matrix_UB_32      0.0240877000
_diffrn_orient_matrix_UB_33      -0.0822710000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0534
_diffrn_reflns_av_unetI/netI     0.0479
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            35634
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        66.747
_diffrn_reflns_theta_max         66.747
_diffrn_reflns_theta_min         4.335
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.218
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78164
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.580
_exptl_crystal_description       needle
_exptl_crystal_F_000             2560
_exptl_crystal_size_max          0.228
_exptl_crystal_size_mid          0.072
_exptl_crystal_size_min          0.072
_refine_diff_density_max         4.545
_refine_diff_density_min         -0.778
_refine_diff_density_rms         0.165
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.173
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     675
_refine_ls_number_reflns         9404
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.173
_refine_ls_R_factor_all          0.1002
_refine_ls_R_factor_gt           0.0873
_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^)+(0.0832P)^2^+52.4304P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2170
_refine_ls_wR_factor_ref         0.2249
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7891
_reflns_number_total             9404
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ce00975e2.cif
_cod_data_source_block           9_BrC2
_cod_database_code               7228487
_chemical_oxdiff_formula         'C24 H28 N6 O4 Br1'
_reflns_odcompleteness_completeness 99.63
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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:
 O4(H4), O6(H6), O13(H13), O18(H18), O20(H20), O27(H27)
2.b Ternary CH refined with riding coordinates:
 C7(H7), C14(H14), C21(H21), C28(H28)
2.c Secondary CH2 refined with riding coordinates:
 C29(H29A,H29B), C32(H32A,H32B), C34(H34A,H34B), C36(H36A,H36B)
2.d Aromatic/amide H refined with riding coordinates:
 C2(H2), C9(H9), C16(H16), C23(H23), C37(H37), C38(H38), C39(H39), C40(H40),
 C43(H43), C44(H44), C45(H45), C46(H46), C47(H47), C48(H48), C51(H51), C52(H52),
  C53(H53), C54(H54)
2.e Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C), C31(H31A,H31B,H31C), C33(H33A,H33B,H33C), C35(H35A,H35B,
 H35C), C55(H55A,H55B,H55C), C57(H57A,H57B,H57C)
2.f Idealised tetrahedral OH refined as rotating group:
 O11(H11), O25(H25)
;
_shelx_res_checksum              17599
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.206
_oxdiff_exptl_absorpt_empirical_full_min 0.797