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_2242130
_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>R</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   geom
_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            8
_cell_length_a                   8.1529(13)
_cell_length_b                   18.185(3)
_cell_length_c                   26.860(4)
_cell_measurement_reflns_used    7498
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.2964
_cell_measurement_theta_min      2.2399
_cell_volume                     3982.3(11)
_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 0.990
_diffrn_measured_fraction_theta_max 0.962
_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  0.0754
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            38240
_diffrn_reflns_theta_full        28.500
_diffrn_reflns_theta_max         29.139
_diffrn_reflns_theta_min         1.352
_exptl_absorpt_coefficient_mu    2.090
_exptl_absorpt_correction_T_max  0.92
_exptl_absorpt_correction_T_min  0.70
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(<i>SADABS</i>; Bruker, 2016)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       column
_exptl_crystal_F_000             1840
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.920
_refine_diff_density_min         -0.342
_refine_ls_abs_structure_details
;
Flack <i>x</i> determined using 2575 quotients
[(<i>I</i>^+^)-(<i>I</i>^-^)]/[(<i>I</i>^+^)+(<i>I</i>^-^)
(Parsons <i>et al.</i>, 2013)
;
_refine_ls_abs_structure_Flack   -0.002(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.968
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     527
_refine_ls_number_reflns         10174
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.968
_refine_ls_R_factor_all          0.0778
_refine_ls_R_factor_gt           0.0445
_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^)+(0.0089P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0848
_refine_ls_wR_factor_ref         0.0934
_reflns_number_gt                7285
_reflns_number_total             10174
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            sj5518sup1.cif
_cod_data_source_block           5
_cod_database_code               2242130
_cod_database_fobs_code          2242130
_shelx_estimated_absorpt_t_min   0.612
_shelx_estimated_absorpt_t_max   0.921
_shelx_hkl_checksum              88648
_shelx_res_checksum              24838