Dynamic and solid-state behaviour of bromoisotrianglimine.
Scholes, Abbie M.; Kershaw Cook, Laurence J.; Szczypiński, Filip T; Luzyanin, Konstantin V.; Egleston, Benjamin D.; Greenaway, Rebecca L.; Slater, Anna G.; Chemical science 15 (2024) 14254–14263; doi:10.1039/d4sc04207g

data_1572333
_publ_section_title
;
 Dynamic and solid-state behaviour of bromoisotrianglimine.
;
_journal_issue                   35
_journal_name_full               'Chemical science'
_journal_page_first              14254
_journal_page_last               14263
_journal_paper_doi               10.1039/d4sc04207g
_journal_volume                  15
_journal_year                    2024
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C42 H45 Br3 N6, C8 H10'
_chemical_formula_sum            'C50 H55 Br3 N6'
_chemical_formula_weight         979.73
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2022-11-16
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-12-07 deposited with the CCDC.	2024-07-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.809(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.0644(2)
_cell_length_b                   14.2714(2)
_cell_length_c                   15.6724(3)
_cell_measurement_reflns_used    34321
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      28.1670
_cell_measurement_theta_min      1.9170
_cell_volume                     2328.31(8)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_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    -40.00  94.00   1.00   10.00    --    5.00  38.00 150.00  134
  2  \w    -46.00  80.00   1.00   10.00    --   -8.90  68.00 120.00  126
  3  \w    -44.00  80.00   1.00   10.00    --   -8.90  57.00 -60.00  124
  4  \w    -44.00  80.00   1.00   10.00    --   -8.90  57.00  60.00  124
  5  \w    -98.00  28.00   1.00   10.00    --   -8.90 -68.00 120.00  126
  6  \w    -44.00  80.00   1.00   10.00    --   -8.90  57.00-150.00  124
  7  \w    -46.00  74.00   1.00   10.00    --   -8.90  68.00   0.00  120
  8  \w    -98.00  28.00   1.00   10.00    --   -8.90 -68.00 -30.00  126
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RCD3): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0679521000
_diffrn_orient_matrix_UB_12      -0.0038529000
_diffrn_orient_matrix_UB_13      0.0158599000
_diffrn_orient_matrix_UB_21      0.0051817000
_diffrn_orient_matrix_UB_22      0.0470023000
_diffrn_orient_matrix_UB_23      0.0156112000
_diffrn_orient_matrix_UB_31      -0.0010994000
_diffrn_orient_matrix_UB_32      -0.0157123000
_diffrn_orient_matrix_UB_33      0.0426298000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            67243
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.303
_diffrn_reflns_theta_min         1.956
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku 007HF (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.639
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82015
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
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    1.397
_exptl_crystal_description       block
_exptl_crystal_F_000             1004
_exptl_crystal_preparation
'Slow vapour diffusion of petroleum ether into a mixed xylenes solution of the compound.'
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.560
_refine_diff_density_min         -0.424
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details
;
 Flack x determined using 4503 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.0093(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     612
_refine_ls_number_reflns         11279
_refine_ls_number_restraints     66
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0320
_refine_ls_R_factor_gt           0.0271
_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^)+(0.0253P)^2^+0.7966P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0529
_refine_ls_wR_factor_ref         0.0541
_reflns_Friedel_coverage         0.891
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.956
_reflns_number_gt                10491
_reflns_number_total             11279
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc04207g2.cif
_cod_data_source_block           33-rr_xylenes_w0003_xylpet_100k_1
_cod_depositor_comments
'Adding full bibliography for 1572326--1572335.cif.'
_cod_original_cell_volume        2328.30(7)
_cod_database_code               1572333
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C50 H55 Br3 N6'
_shelx_estimated_absorpt_t_max   0.817
_shelx_estimated_absorpt_t_min   0.547
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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
 C59-C54 = C52-C58
 1.5 with sigma of 0.02
 C63-C67 = C60-C66
 1.5 with sigma of 0.02
 C68-C74 = C73-C75
 1.5 with sigma of 0.02
 C54-C55 \\sim C55-C56 \\sim C56-C57 \\sim C57-C52 \\sim C52-C53 \\sim C54-C53
 with sigma of 0.01
 C63-C64 \\sim C64-C65 \\sim C65-C60 \\sim C60-C61 \\sim C61-C62 \\sim C63-C62
 with sigma of 0.01
 C68-C69 \\sim C69-C70 \\sim C70-C71 \\sim C71-C72 \\sim C72-C73 \\sim C68-C73
 with sigma of 0.01
3. Restrained planarity
 C54, C53, C59, C55, C52, C56, C57
 with sigma of 0.1
 C63, C61, C62, C60, C65, C66, C64, C67
 with sigma of 0.1
 C68, C69, C74, C73, C70, C75, C72, C71
 with sigma of 0.1
4. Others
 Fixed Sof: C54(0.55) C57(0.55) H57(0.55) C53(0.55) H53(0.55) C59(0.55)
 H59A(0.55) H59B(0.55) H59C(0.55) C52(0.55) C56(0.55) H56(0.55) C55(0.55)
 H55(0.55) C58(0.55) H58A(0.55) H58B(0.55) H58C(0.55) C61(0.27) H61(0.27)
 C62(0.27) H62(0.27) C65(0.27) H65(0.27) C60(0.27) C64(0.27) H64(0.27)
 C66(0.27) H66A(0.27) H66B(0.27) H66C(0.27) C67(0.27) H67A(0.27) H67B(0.27)
 H67C(0.27) C63(0.27) C68(0.18) C69(0.18) H69(0.18) C74(0.18) H74A(0.18)
 H74B(0.18) H74C(0.18) C71(0.18) H71(0.18) C75(0.18) H75A(0.18) H75B(0.18)
 H75C(0.18) C73(0.18) C70(0.18) H70(0.18) C72(0.18) H72(0.18)
5.a Ternary CH refined with riding coordinates:
 C27(H27), C45(H45), C44(H44), C11(H11), C28(H28), C10(H10)
5.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C14(H14A,H14B), C12(H12A,H12B), C32(H32A,H32B), C49(H49A,
 H49B), C13(H13A,H13B), C30(H30A,H30B), C29(H29A,H29B), C46(H46A,H46B),
 C47(H47A,H47B), C31(H31A,H31B), C48(H48A,H48B)
5.c Aromatic/amide H refined with riding coordinates:
 C34(H34), C51(H51), C42(H42), C17(H17), C3(H3), C37(H37), C8(H8), C20(H20),
 C22(H22), C25(H25), C24(H24), C39(H39), C5(H5), C41(H41), C7(H7), C57(H57),
 C53(H53), C56(H56), C55(H55), C61(H61), C62(H62), C65(H65), C64(H64), C69(H69),
  C71(H71), C70(H70), C72(H72)
5.d Idealised Me refined as rotating group:
 C59(H59A,H59B,H59C), C58(H58A,H58B,H58C), C66(H66A,H66B,H66C), C67(H67A,H67B,
 H67C), C74(H74A,H74B,H74C), C75(H75A,H75B,H75C)
;
_shelx_res_checksum              70375
_shelx_hkl_checksum              44809
_olex2_date_sample_data_collection 2022-03-03
_olex2_submission_original_sample_id 'AMS391 Xylene Pet 100 K'
_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 1.231
_oxdiff_exptl_absorpt_empirical_full_min 0.821