Crystal structure of (E)-2-(((6-bromopyridin-2-yl)methylene)amino)-3′,6′-bis(ethylamino)-2′,7′-dimethylspiro[isoindoline-1,9′-xanthen]-3-one—methanol (1:1), C32H30N5O2Br ⋅ CH4O
Xing, Ai-Ping; Zeng, Dai; Zeitschrift für Kristallographie - New Crystal Structures 234 (2019) 599–601; doi:10.1515/ncrs-2018-0500

data_8105793
_publ_section_title
;
 Crystal structure of
 (E)-2-(((6-bromopyridin-2-yl)methylene)amino)-3&#x2032;,6&#x2032;-bis(ethylamino)-2&#x2032;,7&#x2032;-dimethylspiro[isoindoline-1,9&#x2032;-xanthen]-3-one---methanol
 (1:1), C32H30N5O2Br &#x22C5; CH4O
;
_journal_issue                   4
_journal_name_full
'Zeitschrift f\"ur Kristallographie - New Crystal Structures'
_journal_page_first              599
_journal_page_last               601
_journal_paper_doi               10.1515/ncrs-2018-0500
_journal_volume                  234
_journal_year                    2019
_chemical_formula_moiety         'C32 H30 Br N5 O2, C H4 O'
_chemical_formula_sum            'C33 H34 Br N5 O3'
_chemical_formula_weight         628.56
_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   mixed
_cell_angle_alpha                91.187(3)
_cell_angle_beta                 95.764(2)
_cell_angle_gamma                102.256(2)
_cell_formula_units_Z            2
_cell_length_a                   9.1179(2)
_cell_length_b                   9.3291(3)
_cell_length_c                   18.4706(6)
_cell_measurement_reflns_used    7889
_cell_measurement_temperature    105.7(5)
_cell_measurement_theta_max      71.3020
_cell_measurement_theta_min      4.7920
_cell_volume                     1526.14(8)
_computing_cell_refinement       'CrysAlis^Pro^ [1] 2018)'
_computing_data_collection       'CrysAlis^Pro^ [1] 2018)'
_computing_data_reduction        'CrysAlis^Pro^ [1]2018)'
_computing_molecular_graphics    'Olex2 [2]'
_computing_publication_material  'Olex2 [2]'
_computing_structure_refinement  'ShelXL-2015 [3]'
_computing_structure_solution    'ShelXT-2015 [4]'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      105.7(5)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2137
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.964
_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    -62.00  24.00   1.00    2.00    --  -40.81  38.00  30.00   86
  2  \w    -65.00  32.00   1.00    2.00    --  -40.81  38.00 -90.00   97
  3  \w   -104.00 -19.00   1.00    2.00    --  -40.81 -38.00  90.00   85
  4  \w     14.00  78.00   1.00    2.00    --   40.81 -99.00  30.00   64
  5  \w     78.00 166.00   1.00    3.00    --  100.91  30.00 -90.00   88
  6  \w     63.00  89.00   1.00    3.00    --  100.91 -30.00-150.00   26
  7  \w     50.00 126.00   1.00    3.00    --  100.91 -30.00  30.00   76
  8  \w     35.00  90.00   1.00    3.00    --  100.91 -95.00-180.00   55
  9  \w     85.00 138.00   1.00    3.00    --  100.91  30.00-150.00   53
 10  \w     95.00 166.00   1.00    3.00    --  100.91 125.00  90.00   71
 11  \w    146.00 172.00   1.00    3.00    --  100.91 125.00-120.00   26
 12  \w     32.00  82.00   1.00    3.00    --  100.91 -95.00  90.00   50
 13  \w     29.00 127.00   1.00    3.00    --  100.91 -30.00 -60.00   98
 14  \w     87.00 112.00   1.00    3.00    --  100.91-125.00 -60.00   25
 15  \w     36.00 119.00   1.00    3.00    --  100.91 -61.00-180.00   83
 16  \w     60.00 118.00   1.00    3.00    --  100.91-125.00  60.00   58
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0427825000
_diffrn_orient_matrix_UB_12      -0.1270178000
_diffrn_orient_matrix_UB_13      0.0511570000
_diffrn_orient_matrix_UB_21      -0.0147377000
_diffrn_orient_matrix_UB_22      -0.1116099000
_diffrn_orient_matrix_UB_23      -0.0643774000
_diffrn_orient_matrix_UB_31      0.1679133000
_diffrn_orient_matrix_UB_32      -0.0044100000
_diffrn_orient_matrix_UB_33      0.0167078000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0194
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            10106
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.434
_diffrn_reflns_theta_min         4.817
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.171
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66682
_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 light yellow'
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_description       plate
_exptl_crystal_F_000             652
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.921
_refine_diff_density_min         -0.668
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     389
_refine_ls_number_reflns         5746
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0357
_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^)+(0.0513P)^2^+1.0386P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0942
_refine_ls_wR_factor_ref         0.0954
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5452
_reflns_number_total             5746
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            suppl_ncrs-2018-0500_suppl.cif
_cod_data_source_block           1
_cod_original_cell_volume        1526.15(8)
_cod_database_code               8105793
_chemical_oxdiff_formula         'C H N O Br'
_reflns_odcompleteness_completeness 99.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C29(H29A,H29B), C31(H31A,H31B)
2.b Aromatic/amide H refined with riding coordinates:
 N5(H5), C6(H6), C22(H22), C16(H16), C12(H12), C25(H25), C11(H11), C19(H19),
 C4(H4A), C9(H9), C10(H10), C3(H3), C2(H2)
2.c Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C), C27(H27A,H27B,H27C), C30(H30A,H30B,H30C), C33(H33A,H33B,
 H33C), C32(H32A,H32B,H32C)
2.d Idealised tetrahedral OH refined as rotating group:
 O3(H3A)
;
_shelx_res_checksum              57315
_shelx_hkl_checksum              70052
_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 1.460
_oxdiff_exptl_absorpt_empirical_full_min 0.636