Crystal structure of (E)-2-(((6-bromopyridin-2-yl)methylene)amino)-3′,6′-bis(diethylamino)spiro[isoindoline-1,9′-xanthen]-3-one, C34H34N5O2Br
Xing, Ai-Ping; Zeng, Dai; Wang, Xin-Ling; Zeitschrift für Kristallographie - New Crystal Structures 234 (2019) 309–311; doi:10.1515/ncrs-2018-0365

data_8105626
_publ_section_title
;
 Crystal structure of
 (E)-2-(((6-bromopyridin-2-yl)methylene)amino)-3&#x2032;,6&#x2032;-bis(diethylamino)spiro[isoindoline-1,9&#x2032;-xanthen]-3-one,
 C34H34N5O2Br
;
_journal_issue                   2
_journal_name_full
'Zeitschrift f\"ur Kristallographie - New Crystal Structures'
_journal_page_first              309
_journal_page_last               311
_journal_paper_doi               10.1515/ncrs-2018-0365
_journal_volume                  234
_journal_year                    2019
_chemical_formula_moiety         'C34 H34 Br N5 O2'
_chemical_formula_sum            'C34 H34 Br N5 O2'
_chemical_formula_weight         624.57
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.36266(13)
_cell_length_b                   11.83583(8)
_cell_length_c                   12.09985(9)
_cell_measurement_reflns_used    29827
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      76.2110
_cell_measurement_theta_min      4.1060
_cell_volume                     3059.38(4)
_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-2015 [3]'
_computing_structure_solution    'ShelXT-2015 [4]'
_diffrn_ambient_temperature      173.15
_diffrn_detector_area_resol_mean 5.2137
_diffrn_detector_type            AtlasS2
_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    -72.00  23.00   1.00    2.00    --  -40.56  77.00  60.00   95
  2  \w   -101.00 -69.00   1.00    2.00    --  -40.56-143.00  13.00   32
  3  \w    -69.00  22.00   1.00    2.00    --  -40.56  57.00 -30.00   91
  4  \w     10.00  66.00   1.00    2.00    --   40.56  77.00 -90.00   56
  5  \w      8.00 116.00   1.00    2.00    --   40.56  77.00  60.00  108
  6  \w    -32.00  36.00   1.00    2.00    --   40.56 -38.00-180.00   68
  7  \w     67.00 113.00   1.00    2.00    --   40.56  77.00-150.00   46
  8  \w     36.00  98.00   1.00    2.00    --   40.56-128.00-176.00   62
  9  \w     19.00 111.00   1.00    2.00    --   40.56  38.00 -30.00   92
 10  \w      8.00 117.00   1.00    2.00    --   40.56  77.00 150.00  109
 11  \w      8.00  64.00   1.00    2.00    --   40.56  77.00-150.00   56
 12  \w      8.00  95.00   1.00    2.00    --   40.56  77.00   0.00   87
 13  \w     12.00  64.00   1.00    2.00    --   40.56  57.00 150.00   52
 14  \w     38.00  65.00   1.00   10.50    --  111.58-125.00 -90.00   27
 15  \w     82.00 146.00   1.00   10.50    --  111.58  61.00 120.00   64
 16  \w     82.00 108.00   1.00   10.50    --  111.58  61.00-180.00   26
 17  \w     82.00 166.00   1.00   10.50    --  111.58  61.00 -90.00   84
 18  \w     79.00 175.00   1.00   10.50    --  111.58  77.00-180.00   96
 19  \w     44.00 107.00   1.00   10.50    --  111.58 -95.00  30.00   63
 20  \w     82.00 176.00   1.00   10.50    --  111.58  61.00-120.00   94
 21  \w     79.00 105.00   1.00   10.50    --  111.58  77.00  90.00   26
 22  \w     82.00 174.00   1.00   10.50    --  111.58  61.00 150.00   92
 23  \w    114.00 177.00   1.00   10.50    --  111.58  77.00 -30.00   63
 24  \w     82.00 109.00   1.00   10.50    --  111.58  61.00   0.00   27
 25  \w     82.00 108.00   1.00   10.50    --  111.58  61.00  60.00   26
 26  \w     82.00 109.00   1.00   10.50    --  111.58  61.00 -60.00   27
 27  \w     79.00 105.00   1.00   10.50    --  111.58  77.00 -30.00   26
 28  \w     79.00 109.00   1.00   10.50    --  111.58  77.00   0.00   30
 29  \w     79.00 175.00   1.00   10.50    --  111.58  77.00 -60.00   96
 30  \w     30.00 104.00   1.00   10.50    --  111.58 -95.00  90.00   74
 31  \w     79.00 105.00   1.00   10.50    --  111.58  77.00-120.00   26
 32  \w     79.00 106.00   1.00   10.50    --  111.58  77.00 -90.00   27
 33  \w     82.00 177.00   1.00   10.50    --  111.58  61.00  30.00   95
 34  \w     79.00 175.00   1.00   10.50    --  111.58  77.00  60.00   96
 35  \w     82.00 108.00   1.00   10.50    --  111.58  61.00 -30.00   26
 36  \w     79.00 169.00   1.00   10.50    --  111.58  77.00 120.00   90
 37  \w     42.00  91.00   1.00   10.50    --  111.58 -95.00 -90.00   49
 38  \w     79.00 105.00   1.00   10.50    --  111.58  77.00 150.00   26
 39  \w     82.00 108.00   1.00   10.50    --  111.58  61.00  90.00   26
 40  \w     80.00 105.00   1.00   10.50    --  111.58  77.00  30.00   25
 41  \w    132.00 158.00   1.00   10.50    --  111.58  61.00-150.00   26
 42  \w     83.00 108.00   1.00   10.50    --  111.58  61.00-150.00   25
 43  \w     92.00 118.00   1.00   10.50    --  111.58-125.00 -90.00   26
 44  \w     79.00 105.00   1.00   10.50    --  111.58  77.00-150.00   26
 45  \w     36.00 133.00   1.00   10.50    --  111.58 -77.00 120.00   97
 46  \w     30.00 105.00   1.00   10.50    --  111.58 -95.00 -30.00   75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_unetI/netI     0.0153
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            44776
_diffrn_reflns_point_group_measured_fraction_full 0.930
_diffrn_reflns_point_group_measured_fraction_max 0.930
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.994
_diffrn_reflns_theta_min         3.735
_exptl_absorpt_coefficient_mu    2.138
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49457
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_description       needle
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.979
_refine_diff_density_min         -1.035
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.00(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     383
_refine_ls_number_reflns         5403
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0512
_refine_ls_R_factor_gt           0.0507
_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^)+(0.0868P)^2^+2.2969P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1394
_refine_ls_wR_factor_ref         0.1401
_reflns_Friedel_coverage         0.767
_reflns_Friedel_fraction_full    0.852
_reflns_Friedel_fraction_max     0.852
_reflns_number_gt                5322
_reflns_number_total             5403
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            suppl_ncrs-2018-0365_suppl.cif
_cod_data_source_block           1
_cod_database_code               8105626
_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.a Secondary CH2 refined with riding coordinates:
 C27(H27A,H27B), C29(H29A,H29B), C31(H31A,H31B), C33(H33A,H33B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12),
 C16(H16), C17(H17), C19(H19), C22(H22), C24(H24), C25(H25)
2.c Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C), C30(H30A,H30B,H30C), C32(H32A,H32B,H32C), C34(H34A,H34B,
 H34C)
;