Crystal structure of (4′E)-6′-(diethylamino)-2-[(E)-[(6-methylpyridin-2-yl)methylidene]amino]-4′-{2-[(2E)-1,3,3-trimethyl-2,3-dihydro-1H-indol-2-ylidene]ethylidene}-1′,2,2′,3,3′,4′-hexahydrospiro[isoindole-1,9′-xanthene]-3-one, C44H45N5O2
Li, Kaihao; Wu, Jinping; Lan, Hairong; Wang, Junmin; Yuan, Juan; Zeitschrift für Kristallographie - New Crystal Structures 237 (2022) 51–54; doi:10.1515/ncrs-2021-0363

data_8104958
_publ_section_title
;
 Crystal structure of
 (4&#x2032;E)-6&#x2032;-(diethylamino)-2-[(E)-[(6-methylpyridin-2-yl)methylidene]amino]-4&#x2032;-{2-[(2E)-1,3,3-trimethyl-2,3-dihydro-1H-indol-2-ylidene]ethylidene}-1&#x2032;,2,2&#x2032;,3,3&#x2032;,4&#x2032;-hexahydrospiro[isoindole-1,9&#x2032;-xanthene]-3-one,
 C44H45N5O2
;
_journal_issue                   1
_journal_name_full
'Zeitschrift f\"ur Kristallographie - New Crystal Structures'
_journal_page_first              51
_journal_page_last               54
_journal_paper_doi               10.1515/ncrs-2021-0363
_journal_volume                  237
_journal_year                    2022
_chemical_formula_moiety         'C44 H45 N5 O2'
_chemical_formula_sum            'C44 H45 N5 O2'
_chemical_formula_weight         675.85
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_cell_angle_alpha                98.879(3)
_cell_angle_beta                 102.025(3)
_cell_angle_gamma                91.122(3)
_cell_formula_units_Z            2
_cell_length_a                   11.2140(4)
_cell_length_b                   11.9932(5)
_cell_length_c                   14.2703(5)
_cell_measurement_reflns_used    4412
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.3180
_cell_measurement_theta_min      4.0120
_cell_volume                     1851.97(12)
_computing_cell_refinement       'CrysAlis^Pro^ [1]'
_computing_data_collection       'CrysAlis^Pro^ [1]'
_computing_data_reduction        'CrysAlis^Pro^ [1]'
_computing_molecular_graphics    'Olex2 [2]'
_computing_publication_material  'Olex2 [2]'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015) [3]'
_computing_structure_solution    'ShelXT-2015 [4]'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_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   -108.00 -33.00   0.60    5.00    --  -33.50 178.00  30.00  125
  2  \w    -80.00  -9.80   0.60    5.00    --  -33.50 -77.00  30.00  117
  3  \w   -101.00 -68.00   0.60    5.00    --  -33.50 -57.00 -90.00   55
  4  \w     51.80  77.00   0.60    5.00    --   36.47 -99.00  90.00   42
  5  \w     33.60 104.40   0.60    5.00    --   36.47  57.00  90.00  118
  6  \w     60.00  89.40   0.60    5.00    --   36.47 178.00  90.00   49
  7  \w     48.00  93.60   0.60    5.00    --   36.47  37.00   0.00   76
  8  \w     -1.00  76.40   0.60    5.00    --   36.47 -99.00-180.00  129
  9  \w     31.00  88.00   0.60    5.00    --   36.47  57.00-120.00   95
 10  \w    -32.00  54.40   0.60    5.00    --   36.47 -57.00 -60.00  144
 11  \w     10.00  44.20   0.60    5.00    --   36.47  77.00   0.00   57
 12  \w     -8.00  62.20   0.60    5.00    --   36.47 -77.00-120.00  117
 13  \w     -3.00  22.20   0.60    5.00    --   36.47 -99.00  90.00   42
 14  \w     71.00  97.40   0.60    5.00    --   36.47  57.00 150.00   44
 15  \w     66.00 104.40   0.60    5.00    --   36.47  77.00   0.00   64
 16  \w     85.00 173.20   0.60   22.50    --  108.00  77.00-180.00  147
 17  \w    102.00 171.60   0.60   22.50    --  108.00  61.00 -60.00  116
 18  \w    103.00 145.00   0.60   22.50    --  108.00 111.00  30.00   70
 19  \w     63.00 105.60   0.60   22.50    --  108.00 -94.00 120.00   71
 20  \w     55.00 109.60   0.60   22.50    --  108.00-111.00  90.00   91
 21  \w     38.00 110.00   0.60   22.50    --  108.00 -94.00 -90.00  120
 22  \w     38.00 127.40   0.60   22.50    --  108.00 -45.00-120.00  149
 23  \w     41.00 104.00   0.60   22.50    --  108.00 -61.00 120.00  105
 24  \w     89.00 146.00   0.60   22.50    --  108.00  45.00  90.00   95
 25  \w     39.00  78.60   0.60   22.50    --  108.00 -77.00  90.00   66
 26  \w    104.00 152.00   0.60   22.50    --  108.00  61.00 -30.00   80
 27  \w     87.00 144.60   0.60   22.50    --  108.00 178.00 120.00   96
 28  \w     70.00 112.00   0.60   22.50    --  108.00-111.00-120.00   70
 29  \w    119.00 145.40   0.60   22.50    --  108.00 111.00 150.00   44
 30  \w    117.00 174.60   0.60   22.50    --  108.00  61.00 -90.00   96
 31  \w     79.00 173.20   0.60   22.50    --  108.00  77.00-150.00  157
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0922087000
_diffrn_orient_matrix_UB_12      0.0893689000
_diffrn_orient_matrix_UB_13      -0.0272049000
_diffrn_orient_matrix_UB_21      -0.0763960000
_diffrn_orient_matrix_UB_22      -0.0361700000
_diffrn_orient_matrix_UB_23      0.0693661000
_diffrn_orient_matrix_UB_31      0.0738038000
_diffrn_orient_matrix_UB_32      0.0875002000
_diffrn_orient_matrix_UB_33      0.0834259000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13570
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.067
_diffrn_reflns_theta_max         67.067
_diffrn_reflns_theta_min         3.736
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.589
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92212
_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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.212
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     476
_refine_ls_number_reflns         6625
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0716
_refine_ls_R_factor_gt           0.0549
_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^)+(0.0832P)^2^+0.3616P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1456
_refine_ls_wR_factor_ref         0.1616
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5090
_reflns_number_total             6625
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            suppl_j_ncrs-2021-0363_suppl.cif
_cod_data_source_block           1
_cod_original_cell_volume        1851.98(12)
_cod_database_code               8104958
_chemical_oxdiff_formula         C30H3O5N2
_chemical_oxdiff_usercomment     r
_shelx_estimated_absorpt_t_max   0.954
_shelx_estimated_absorpt_t_min   0.927
_reflns_odcompleteness_completeness 99.91
_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
 C13A-C12A
 1.54 with sigma of 0.02
 C12A-C11A
 1.54 with sigma of 0.02
 C8-C13A
 1.54 with sigma of 0.02
 C13-C12
 1.54 with sigma of 0.02
 C11-C12
 1.54 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C12) = Uanis(C12A)
Uanis(C13) = Uanis(C13A)
Uanis(C11) = Uanis(C11A)
4. Others
 Sof(C12A)=Sof(H12C)=Sof(H12D)=Sof(C13A)=Sof(H13C)=Sof(H13D)=Sof(C11A)=
 Sof(H11C)=Sof(H11D)=1-FVAR(1)
 Sof(C11)=Sof(H11A)=Sof(H11B)=Sof(C12)=Sof(H12A)=Sof(H12B)=Sof(C13)=Sof(H13A)=
 Sof(H13B)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B), C41(H41A,H41B), C43(H43A,
 H43B), C12A(H12C,H12D), C13A(H13C,H13D), C11A(H11C,H11D)
5.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21),
 C23(H23), C24(H24), C25(H25), C28(H28), C29(H29), C34(H34), C35(H35), C36(H36),
  C37(H37)
5.c Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C), C38(H38A,H38B,H38C), C39(H39A,H39B,H39C), C40(H40A,H40B,
 H40C), C42(H42A,H42B,H42C), C44(H44A,H44B,H44C)
;