Crystal structure of (Z)-2-(tert-butyl)-5-((5-(tert- butyl)-2H-pyrrol-2-ylidene)(mesityl)methyl)-1H-pyrrole, C26H34N2
Liu, Yingfan; Zhao, Zhiqiang; Zeitschrift für Kristallographie - New Crystal Structures 237 (2022) 971–974; doi:10.1515/ncrs-2022-0307

data_8107267
_publ_section_title
;
 Crystal structure of (Z)-2-(tert-butyl)-5-((5-(tert-
 butyl)-2H-pyrrol-2-ylidene)(mesityl)methyl)-1H-pyrrole, C26H34N2
;
_journal_issue                   5
_journal_name_full
'Zeitschrift f\"ur Kristallographie - New Crystal Structures'
_journal_page_first              971
_journal_page_last               974
_journal_paper_doi               10.1515/ncrs-2022-0307
_journal_volume                  237
_journal_year                    2022
_chemical_formula_moiety         'C26 H34 N2'
_chemical_formula_sum            'C26 H34 N2'
_chemical_formula_weight         374.55
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.8062(2)
_cell_length_b                   15.8918(2)
_cell_length_c                   20.0121(3)
_cell_measurement_reflns_used    5405
_cell_measurement_temperature    296.2(5)
_cell_measurement_theta_max      69.2850
_cell_measurement_theta_min      3.7160
_cell_volume                     4708.79(11)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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      air
_diffrn_ambient_temperature      296.2(5)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0528
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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     38.00  79.00   1.00    1.00    --   23.56 -99.00  90.00   41
  2  \w     10.00  36.00   1.00    1.00    --   23.56 -99.00  90.00   26
  3  \w     51.00  95.00   1.00   15.00    --  115.13-104.00  30.00   44
  4  \w    129.00 159.00   1.00   15.00    --  115.13 -11.00 150.00   30
  5  \w    112.00 138.00   1.00   15.00    --  115.13 103.00  55.00   26
  6  \w    101.00 145.00   1.00    3.00    --   69.34 111.00  60.00   44
  7  \w    112.00 156.00   1.00    3.00    --   69.34 111.00 120.00   44
  8  \w     88.00 176.00   1.00   15.00    --  115.13 138.00 120.00   88
  9  \w    103.00 152.00   1.00    3.00    --   69.34 111.00 -60.00   49
 10  \w    108.00 145.00   1.00   15.00    --  115.13 104.00-120.00   37
 11  \w     65.00 172.00   1.00   15.00    --  115.13  43.00 -30.00  107
 12  \w     25.00 102.00   1.00   15.00    --  115.13 -11.00 150.00   77
 13  \w    -26.00  -1.00   1.00    1.00    --   23.56 108.00 -41.00   25
 14  \w    -84.00 -59.00   1.00    3.00    --  -69.34 111.00   0.00   25
 15  \w    -47.00  -7.00   1.00    3.00    --  -69.34 111.00   0.00   40
 16  \w    -95.00  11.00   1.00    1.00    --  -23.56 -57.00 120.00  106
 17  \w   -148.00 -46.00   1.00    3.00    --  -69.34 -50.00  60.00  102
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0996386000
_diffrn_orient_matrix_UB_12      -0.0280585000
_diffrn_orient_matrix_UB_13      -0.0000701000
_diffrn_orient_matrix_UB_21      -0.0067967000
_diffrn_orient_matrix_UB_22      0.0213532000
_diffrn_orient_matrix_UB_23      -0.0749274000
_diffrn_orient_matrix_UB_31      0.0292959000
_diffrn_orient_matrix_UB_32      -0.0902518000
_diffrn_orient_matrix_UB_33      -0.0177277000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0157
_diffrn_reflns_av_unetI/netI     0.0172
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            8907
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        66.592
_diffrn_reflns_theta_max         66.592
_diffrn_reflns_theta_min         4.419
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.460
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65235
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.057
_exptl_crystal_description       block
_exptl_crystal_F_000             1632
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       0.0022(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         4155
_refine_ls_number_restraints     82
_refine_ls_restrained_S_all      1.113
_refine_ls_R_factor_all          0.0608
_refine_ls_R_factor_gt           0.0548
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1022P)^2^+0.6887P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1618
_refine_ls_wR_factor_ref         0.1701
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3592
_reflns_number_total             4155
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            suppl_j_ncrs-2022-0307_suppl.cif
_cod_data_source_block           2
_cod_database_code               8107267
_chemical_oxdiff_formula         'C1 H1 N1'
_shelx_estimated_absorpt_t_max   0.914
_shelx_estimated_absorpt_t_min   0.837
_reflns_odcompleteness_completeness 99.94
_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 N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C14-C15 \\sim C14-C15A
 with sigma of 0.02
 N2-H2A \\sim N1-H1
 with sigma of 0.02
 C14-C16 \\sim C14-C16A
 with sigma of 0.02
 C14-C17 \\sim C14-C17A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C10 \\sim C11 \\sim C12 \\sim C13: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.03 within 2A
Uanis(C16) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.007
Uanis(C15) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(C17) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.01
Uanis(C15A) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Rigid body (RIGU) restrains
 C16, C17, C14, C15
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C17A, C15A, C16A, C14
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C15A, C16A, C17A, C14
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
5. Others
 Sof(H2A)=1-FVAR(1)
 Sof(H1)=FVAR(1)
 Fixed Sof: C15(0.65) H15A(0.65) H15B(0.65) H15C(0.65) C16(0.65) H16A(0.65)
 H16B(0.65) H16C(0.65) C17(0.65) H17A(0.65) H17B(0.65) H17C(0.65) C15A(0.35)
 H15D(0.35) H15E(0.35) H15F(0.35) C16A(0.35) H16D(0.35) H16E(0.35) H16F(0.35)
 C17A(0.35) H17D(0.35) H17E(0.35) H17F(0.35)
6.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C7(H7), C8(H8), C20(H20), C22(H22), N2(H2A)
6.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C15(H15A,H15B,
 H15C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C24(H24A,H24B,H24C), C25(H25A,
 H25B,H25C), C26(H26A,H26B,H26C), C15A(H15D,H15E,H15F), C16A(H16D,H16E,H16F),
 C17A(H17D,H17E,H17F)
;
_shelx_res_checksum              6111
_shelx_hkl_checksum              57809
_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 1.493
_oxdiff_exptl_absorpt_empirical_full_min 0.718