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_1572331
_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, 0.65(C7 H8), C2.45 H2.45'
_chemical_formula_sum            'C49 H52.65 Br3 N6'
_chemical_formula_weight         965.35
_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             2022-09-13
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-12-07 deposited with the CCDC.	2024-07-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.692(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.0041(2)
_cell_length_b                   14.3125(2)
_cell_length_c                   15.5247(3)
_cell_measurement_reflns_used    25294
_cell_measurement_temperature    100.01(11)
_cell_measurement_theta_max      28.1570
_cell_measurement_theta_min      1.9330
_cell_volume                     2302.09(7)
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(11)
_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 0.987
_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    -84.00  40.00   1.00   10.00    --    5.00 -57.00-180.00  124
  2  \w    -46.00  80.00   1.00   10.00    --   -8.90  68.00  90.00  126
  3  \w    -44.00  80.00   1.00   10.00    --   -8.90  57.00 -90.00  124
  4  \w    -44.00  80.00   1.00   10.00    --   -8.90  57.00 -30.00  124
  5  \w    -46.00  80.00   1.00   10.00    --   -8.90  68.00  30.00  126
  6  \w    -98.00   8.00   1.00   10.00    --   -8.90 -57.00 -30.00  106
;
_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      0.0190579000
_diffrn_orient_matrix_UB_12      -0.0006181000
_diffrn_orient_matrix_UB_13      0.0484478000
_diffrn_orient_matrix_UB_21      0.0354265000
_diffrn_orient_matrix_UB_22      -0.0416733000
_diffrn_orient_matrix_UB_23      0.0011003000
_diffrn_orient_matrix_UB_31      0.0553579000
_diffrn_orient_matrix_UB_32      0.0268354000
_diffrn_orient_matrix_UB_33      0.0028620000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_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       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            47561
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.297
_diffrn_reflns_theta_min         1.966
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku 007HF (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.668
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88133
_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            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_description       block
_exptl_crystal_F_000             987
_exptl_crystal_preparation
'Slow vapour diffusion of toluene into an acetonitrile solution.'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.695
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details
;
 Flack x determined using 4342 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.010(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     563
_refine_ls_number_reflns         11043
_refine_ls_number_restraints     29
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0353
_refine_ls_R_factor_gt           0.0303
_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^)+(0.0291P)^2^+1.1077P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0622
_refine_ls_wR_factor_ref         0.0634
_reflns_Friedel_coverage         0.886
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.945
_reflns_number_gt                10218
_reflns_number_total             11043
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc04207g2.cif
_cod_data_source_block           33-rr_tol_w0002_ams384-1_mecntol_100k_1
_cod_depositor_comments
'Adding full bibliography for 1572326--1572335.cif.'
_cod_database_code               1572331
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C49 H53 Br3 N6'
_shelx_estimated_absorpt_t_max   0.776
_shelx_estimated_absorpt_t_min   0.617
_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
 C58B-C52B = C58C-C56B
 1.5 with sigma of 0.02
 C57B-C52B \\sim C52B-C53B \\sim C53B-C54B \\sim C54B-C55B \\sim C55B-C56B
\\sim C57B-C56B
 with sigma of 0.02
 C58B-C53B \\sim C58B-C57B \\sim C58C-C55B \\sim C58C-C57B
 with sigma of 0.02
3. Restrained planarity
 C53B, C57B, C56B, C52B, C55B, C54B, C58B, C58C
 with sigma of 0.1
4. Others
 Fixed Sof: C57A(0.65) H57A(0.65) C55A(0.65) H55A(0.65) C56A(0.65) H56A(0.65)
 C52A(0.65) C54A(0.65) H54A(0.65) C53A(0.65) H53A(0.65) C58A(0.65) H58G(0.65)
 H58H(0.65) H58I(0.65) C52B(0.35) C57B(0.35) H57B(0.35) C54B(0.35) H54B(0.35)
 C53B(0.35) H53B(0.35) C56B(0.35) C55B(0.35) H55B(0.35) C58B(0.18) H58A(0.18)
 H58B(0.18) H58C(0.18) C58C(0.17) H58D(0.17) H58E(0.17) H58F(0.17)
5.a Ternary CH refined with riding coordinates:
 C27(H27), C44(H44), C28(H28), C11(H11), C49(H49), C10(H10)
5.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C15(H15A,H15B), C14(H14A,H14B), C30(H30A,H30B), C48(H48A,
 H48B), C29(H29A,H29B), C32(H32A,H32B), C47(H47A,H47B), C13(H13A,H13B),
 C31(H31A,H31B), C45(H45A,H45B), C46(H46A,H46B)
5.c Aromatic/amide H refined with riding coordinates:
 C34(H34), C17(H17), C8(H8), C51(H51), C20(H20), C22(H22), C37(H37), C39(H39),
 C25(H25), C24(H24), C41(H41), C3(H3), C42(H42), C5(H5), C7(H7), C57A(H57A),
 C55A(H55A), C56A(H56A), C54A(H54A), C53A(H53A), C57B(H57B), C54B(H54B),
 C53B(H53B), C55B(H55B)
5.d Idealised Me refined as rotating group:
 C58A(H58G,H58H,H58I), C58B(H58A,H58B,H58C), C58C(H58D,H58E,H58F)
;
_shelx_res_checksum              99711
_shelx_hkl_checksum              69664
_olex2_date_sample_data_collection 2022-03-03
_olex2_submission_original_sample_id 'AMS384-1 MeCN Tol 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 1.220
_oxdiff_exptl_absorpt_empirical_full_min 0.845