Synthesis, resolution and crystal structures of two enantiomeric rhodamine derivatives
Stephenson, Clifton J.; Mague, Joel T.; Kamm, Nathaniel; Aleman, Nathalie; Rich, Dayla; Dang, Quynh-Nhu; Nguyen, Ha Van; Acta Crystallographica Section E 73 (2017) 327–333; doi:10.1107/S2056989017001451

data_2242129
_publ_section_title
;
 Synthesis, resolution and crystal structures of two enantiomeric
 rhodamine derivatives
;
_journal_coeditor_code           SJ5518
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              327
_journal_page_last               333
_journal_paper_doi               10.1107/S2056989017001451
_journal_volume                  73
_journal_year                    2017
_chemical_formula_iupac          'C24 H20 Br N O3'
_chemical_formula_moiety         'C24 H20 Br N O3'
_chemical_formula_sum            'C24 H20 Br N O3'
_chemical_formula_weight         450.32
_chemical_name_systematic
(1<i>S</i>)-6'-Bromo-3'-diethylamino-3<i>H</i>-spiro[2-benzofuran-1,9'-xanthen]-3-one
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.0772(6)
_cell_length_b                   13.0582(8)
_cell_length_c                   13.8966(8)
_cell_measurement_reflns_used    9874
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.662
_cell_measurement_theta_min      2.411
_cell_volume                     2010.1(2)
_computing_cell_refinement
;
<i>SAINT</i> (Bruker, 2016)
;
_computing_data_collection
;
<i>APEX3</i> (Bruker, 2016)
;
_computing_data_reduction
;
<i>SAINT</i> (Bruker, 2016)
;
_computing_molecular_graphics
;
<i>DIAMOND</i> (Brandenburg & Putz, 2012)
;
_computing_publication_material
;
<i>SHELXTL</i> (Sheldrick, 2008)
;
_computing_structure_refinement
;
<i>SHELXL2014</i> (Sheldrick, 2015<i>b</i>)
;
_computing_structure_solution
;
<i>SHELXT</i> (Sheldrick, 2015<i>a</i>)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0433
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            39006
_diffrn_reflns_theta_full        29.213
_diffrn_reflns_theta_max         29.213
_diffrn_reflns_theta_min         2.140
_exptl_absorpt_coefficient_mu    2.071
_exptl_absorpt_correction_T_max  0.82
_exptl_absorpt_correction_T_min  0.69
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(<i>SADABS</i>; Bruker, 2016)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.488
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       column
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.623
_refine_diff_density_min         -0.249
_refine_ls_abs_structure_details
;
Flack <i>x</i> determined using 1981 quotients
[(<i>I</i>^+^)-(<i>I</i>^-^)]/[(<i>I</i>^+^)+(<i>I</i>^-^)
(Parsons <i>et al.</i>, 2013)
;
_refine_ls_abs_structure_Flack   -0.006(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     320
_refine_ls_number_reflns         5417
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.985
_refine_ls_R_factor_all          0.0299
_refine_ls_R_factor_gt           0.0259
_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^)+(0.0299P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0569
_refine_ls_wR_factor_ref         0.0576
_reflns_number_gt                4926
_reflns_number_total             5417
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            sj5518sup1.cif
_cod_data_source_block           4
_cod_database_code               2242129
_cod_database_fobs_code          2242129
_shelx_estimated_absorpt_t_min   0.566
_shelx_estimated_absorpt_t_max   0.820
_shelx_hkl_checksum              85351
_shelx_res_checksum              23039