Scalable Regioselective Synthesis of Rhodamine Dyes.
Dwight, Stephen J.; Levin, Sergiy; Organic letters 18 (2016) 5316–5319; doi:10.1021/acs.orglett.6b02635

data_1555838
_publ_section_title
;
 Scalable Regioselective Synthesis of Rhodamine Dyes.
;
_journal_issue                   20
_journal_name_full               'Organic letters'
_journal_page_first              5316
_journal_page_last               5319
_journal_paper_doi               10.1021/acs.orglett.6b02635
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C34 H33 Cl N2 O3'
_chemical_formula_sum            'C34 H33 Cl N2 O3'
_chemical_formula_weight         553.07
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-08-14
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.61287(10)
_cell_length_b                   18.37433(20)
_cell_length_c                   18.9503(2)
_cell_measurement_reflns_used    13520
_cell_measurement_temperature    99.8(2)
_cell_measurement_theta_max      74.7240
_cell_measurement_theta_min      3.2820
_cell_volume                     2650.79(5)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.8(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 4.1587
_diffrn_detector_type            Onyx
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
  1 omega   16.00  108.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       41.9419   57.0000   30.0000 92

  2 omega   87.00  115.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       41.9419  125.0000  -60.0000 28

  3 omega   97.00  178.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0000   45.0000 -120.0000 81

  4 omega   97.00  124.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -61.0000  -90.0000 27

  5 omega   80.00  114.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0000 -111.0000  -60.0000 34

  6 omega   75.00  115.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0000 -111.0000   60.0000 40

  7 omega   79.00  114.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0000 -111.0000  120.0000 35

  8 omega   79.00  100.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -77.0000  150.0000 21

  9 omega   59.00  100.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0000   15.0000  120.0000 41

 10 omega   84.00  175.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0000   45.0000  150.0000 91

 11 omega  127.00  175.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0000   15.0000  120.0000 48

 12 omega   80.00  178.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0000   30.0000    0.0000 98

 13 omega   41.00   96.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -94.0000   60.0000 55

 14 omega   36.00   91.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -94.0000  120.0000 55

 15 omega   32.00   57.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0000 -111.0000   60.0000 25

 16 omega   36.00   73.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -94.0000   90.0000 37

 17 omega   36.00   67.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -77.0000  150.0000 31

 18 omega   28.00   96.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -94.0000  150.0000 68

 19 omega   30.00   55.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -30.0000  150.0000 25

 20 omega   30.00   55.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0000 -111.0000  120.0000 25

 21 omega   31.00  113.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0000 -111.0000    0.0000 82

 22 omega   41.00   81.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -61.0000  -90.0000 40

 23 omega   46.00   74.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -45.0000 -150.0000 28

 24 omega   40.00  128.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -61.0000 -180.0000 88

 25 omega   34.00   77.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -45.0000  -30.0000 43

 26 omega   31.00   63.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -30.0000 -120.0000 32

 27 omega   33.00   77.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0000 -111.0000 -150.0000 44

 28 omega   32.00   59.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0000 -111.0000  -60.0000 27

 29 omega    5.00   92.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       41.9419 -125.0000 -180.0000 87

 30 omega  -31.00   67.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       41.9419  -57.0000 -120.0000 98

 31 omega -114.00  -82.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.9419  -99.0000    0.0000 32
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Onyx, Nova'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1471880000
_diffrn_orient_matrix_UB_12      0.0210323000
_diffrn_orient_matrix_UB_13      0.0519474000
_diffrn_orient_matrix_UB_21      0.1387196000
_diffrn_orient_matrix_UB_22      -0.0177878000
_diffrn_orient_matrix_UB_23      -0.0566111000
_diffrn_orient_matrix_UB_31      -0.0079029000
_diffrn_orient_matrix_UB_32      0.0791874000
_diffrn_orient_matrix_UB_33      -0.0265204000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0498
_diffrn_reflns_av_unetI/netI     0.0342
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            25831
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.226
_diffrn_reflns_theta_min         3.350
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Nova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.596
_exptl_absorpt_correction_T_max  0.947
_exptl_absorpt_correction_T_min  0.824
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_description       plank
_exptl_crystal_F_000             1168
_exptl_crystal_recrystallization_method 'Crystallized from DMSO'
_exptl_crystal_size_max          0.2031
_exptl_crystal_size_mid          0.0997
_exptl_crystal_size_min          0.0561
_refine_diff_density_max         1.350
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.102
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.49(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     362
_refine_ls_number_reflns         4853
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0638
_refine_ls_R_factor_gt           0.0616
_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^)+(0.1267P)^2^+0.3651P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1543
_refine_ls_wR_factor_ref         0.1575
_reflns_Friedel_coverage         0.750
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                4630
_reflns_number_total             4853
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b02635_si_008.cif
_cod_data_source_block           cs2213
_cod_database_code               1555838
_chemical_oxdiff_formula         'C34 H33 Cl N2 O3'
_chemical_oxdiff_usercomment     'Laurent Bernad (Promega sample 49438)'
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.51(3) 0.49(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
3.a Secondary CH2 refined with riding coordinates:
 C26(H26A,H26B), C7(H7A,H7B), C16(H16A,H16B), C23(H23A,H23B), C15(H15A,H15B),
 C22(H22A,H22B), C25(H25A,H25B), C27(H27A,H27B), C24(H24A,H24B), C17(H17A,H17B),
  C18(H18A,H18B), C4(H4A,H4B), C6(H6A,H6B), C5(H5A,H5B)
3.b Aromatic/amide H refined with riding coordinates:
 C32(H32), C13(H13), C9(H9), C29(H29), C31(H31)
;
_shelx_res_checksum              76994
_shelx_hkl_checksum              72695
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2015-08-11
_olex2_date_sample_submission    2015-08-10
_olex2_exptl_crystal_mounting_method 'Mounted on Nylon loop with Krytox oil'
_olex2_submission_special_instructions 'No special instructions were received'