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

data_1555832
_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         'C25 H22 N2 O5, 4(H2 O)'
_chemical_formula_sum            'C25 H30 N2 O9'
_chemical_formula_weight         502.51
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2015-09-02
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                101.950(2)
_cell_angle_beta                 109.822(2)
_cell_angle_gamma                95.373(2)
_cell_formula_units_Z            2
_cell_length_a                   9.4188(2)
_cell_length_b                   11.1969(3)
_cell_length_c                   12.4356(3)
_cell_measurement_reflns_used    7997
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.2390
_cell_measurement_theta_min      3.8670
_cell_volume                     1187.75(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    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 4.1587
_diffrn_detector_type            Onyx
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details
;
  1 omega   15.00  111.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       41.9419   57.0000   60.0000 96

  2 omega  103.00  148.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   77.0000   37.1359 45

  3 omega  113.00  146.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       74.0000   77.0000   70.0386 33

  4 omega  119.00  178.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0000   77.0000  120.0000 59

  5 omega  139.00  167.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0000   77.0000  150.0000 28

  6 omega  138.00  175.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0000   61.0000   90.0000 37

  7 omega  130.00  157.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0000   61.0000    0.0000 27

  8 omega  123.00  168.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0000   77.0000  -30.0000 45

  9 omega  121.00  173.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0000   77.0000  -90.0000 52

 10 omega  127.00  154.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0000   77.0000 -150.0000 27

 11 omega  135.00  173.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  111.0000 -180.0000 38

 12 omega  125.00  174.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0000   61.0000 -180.0000 49

 13 omega   98.00  125.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  111.0000 -180.0000 27

 14 omega   79.00  117.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0000   61.0000 -180.0000 38

 15 omega   78.00  158.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0000   61.0000 -120.0000 80

 16 omega   85.00  138.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0000   61.0000  -90.0000 53

 17 omega   82.00  116.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0000   61.0000  -60.0000 34

 18 omega   79.00  142.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0000   61.0000  -30.0000 63

 19 omega  104.00  133.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0000   77.0000   60.0000 29

 20 omega   79.00  178.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0000   61.0000   60.0000 99

 21 omega  116.00  153.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -15.0000   60.0000 37

 22 omega   99.00  126.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -77.0000    0.0000 27

 23 omega   80.00  100.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0000 -112.0000  -76.5396 20

 24 omega   67.00   94.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0000 -111.0000  -30.0000 27

 25 omega   50.00  115.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0000 -111.0000   60.0000 65

 26 omega   48.00  101.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0000 -111.0000  150.0000 53

 27 omega   42.00   87.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -94.0000  150.0000 45

 28 omega   34.00   66.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -45.0000   60.0000 32

 29 omega   37.00   78.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -77.0000    0.0000 41

 30 omega   42.00   69.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -45.0000   30.0000 27

 31 omega   38.00  108.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0000 -111.0000    0.0000 70

 32 omega   31.00   67.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0000 -112.0000  -76.5396 36

 33 omega   30.00   80.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0000 -111.0000 -150.0000 50

 34 omega   42.00  136.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -61.0000 -180.0000 94

 35 omega   80.00  111.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0000   61.0000    0.0000 31

 36 omega   73.00  100.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0000   77.0000   60.0000 27

 37 omega   82.00  137.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0000   61.0000   90.0000 55

 38 omega   79.00  157.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0000   61.0000  150.0000 78

 39 omega   80.00  133.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0000   61.0000  120.0000 53

 40 omega   74.00  107.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0000   77.0000  150.0000 33

 41 omega   74.00  101.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0000   77.0000   90.0000 27

 42 omega   73.00  100.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0000   77.0000  120.0000 27

 43 omega   73.00  138.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0000   77.0000   30.0000 65

 44 omega   73.00  110.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0000   77.0000  -30.0000 37

 45 omega   81.00  100.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0000   77.0000  -90.0000 19

 46 omega   85.00  100.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0000   77.0000 -120.0000 15

 47 omega   79.00  106.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0000   61.0000 -150.0000 27

 48 omega   85.00  156.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       78.0000   76.0000 -131.3278 71

 49 omega   75.00  134.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0000   77.0000 -180.0000 59

 50 omega   74.00  109.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0000   77.0000  -60.0000 35

 51 omega   74.00  175.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0000   77.0000    0.0000 101

 52 omega   85.00  107.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0000   77.0000 -150.0000 22

 53 omega   45.00   61.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       78.0000   76.0000 -131.3278 16

 54 omega   30.00   64.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   76.0000  -94.2039 34

 55 omega   37.00   62.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   77.0000  -53.8253 25

 56 omega   36.00   99.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   77.0000  -16.3386 63

 57 omega   39.00   67.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   77.0000   37.1359 28

 58 omega   40.00   66.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       74.0000   77.0000   70.0386 26

 59 omega   42.00   69.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       74.0000   76.0000  101.2439 27

 60 omega   42.00   76.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       74.0000   75.0000  164.3123 34

 61 omega   32.00   73.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   77.0000  133.6707 41

 62 omega   19.00   44.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   81.0000   93.6704 25

 63 omega   19.00   44.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   80.0000  150.1857 25

 64 omega   19.00   44.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   80.0000   28.0156 25

 65 omega   14.00   78.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       41.9419   37.0000    0.0000 64

 66 omega   26.00   53.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   76.0000  -49.8154 27

 67 omega   27.00   59.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   76.0000 -123.6219 32

 68 omega   35.00   65.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   76.0000 -164.8784 30

 69 omega    9.00   34.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       46.0000   86.0000 -160.8194 25

 70 omega    3.00   28.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       42.0000   90.0000 -125.7581 25

 71 omega  -67.00   30.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.9419   57.0000   30.0000 97

 72 omega  -49.00  -15.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.9419  -57.0000 -120.0000 34

 73 omega -110.00  -75.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.9419  -57.0000 -120.0000 35

 74 omega   26.00   93.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -15.0000   60.0000 67

 75 omega   43.00   89.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -94.0000 -180.0000 46

 76 omega  -98.00   -5.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.9419  125.0000  120.0000 93
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Onyx, Nova'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0927484000
_diffrn_orient_matrix_UB_12      -0.1196424000
_diffrn_orient_matrix_UB_13      -0.0946304000
_diffrn_orient_matrix_UB_21      -0.0701854000
_diffrn_orient_matrix_UB_22      0.0776998000
_diffrn_orient_matrix_UB_23      -0.0868637000
_diffrn_orient_matrix_UB_31      0.1330026000
_diffrn_orient_matrix_UB_32      -0.0086282000
_diffrn_orient_matrix_UB_33      -0.0452415000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0479
_diffrn_reflns_av_unetI/netI     0.0303
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            25369
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.754
_diffrn_reflns_theta_min         3.908
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Nova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.901
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_correction_T_min  0.870
_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            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_description       plank
_exptl_crystal_F_000             532
_exptl_crystal_size_max          0.3368
_exptl_crystal_size_mid          0.0443
_exptl_crystal_size_min          0.0189
_refine_diff_density_max         0.629
_refine_diff_density_min         -0.952
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     365
_refine_ls_number_reflns         4817
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0837
_refine_ls_R_factor_gt           0.0722
_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^)+(0.1379P)^2^+0.6696P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2066
_refine_ls_wR_factor_ref         0.2233
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3925
_reflns_number_total             4817
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b02635_si_006.cif
_cod_data_source_block           cs2215
_cod_original_cell_volume        1187.75(6)
_cod_database_code               1555832
_chemical_oxdiff_formula         'C25 H22 N2 O5 H6 O3'
_chemical_oxdiff_usercomment
'Laurent Bernad (Promega Biosciences sample 49436-TAMRA)'
_reflns_odcompleteness_completeness 99.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2. Restrained distances
 H3-O8B
 1.67 with sigma of 0.04
 H9A-O5_$1
 2.09 with sigma of 0.04
 H9B-O2
 2.09 with sigma of 0.04
 H8B-O3
 1.91 with sigma of 0.04
 H8A-O9A
 1.88 with sigma of 0.04
 H7B-O8A_$1
 1.93 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
O8A \\sim O8B: within 1.7A with sigma of 0.04 and sigma for terminal atoms of
0.08
4. Others
 Fixed Sof: H3(0.5) H4(0.5) O8A(0.5) H8A(0.5) H8B(0.5) O9A(0.5) H9A(0.5)
 H9B(0.5) O8B(0.5) H8C(0.5) H8D(0.5) O9B(0.5) H9C(0.5) H9D(0.5)
5.a Free rotating group:
 O6(H6A,H6B), O7(H7A,H7B), O8A(H8A,H8B), O9A(H9A,H9B), O8B(H8C,H8D), O9B(H9C,
 H9D)
5.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4A), C5(H5), C9(H9), C10(H10), C12(H12), C18(H18), C19(H19),
 C21(H21)
5.c Tetrahedral OH refined with riding coordinates:
 O3(H3), O4(H4)
5.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C24(H24A,H24B,H24C), C25(H25A,H25B,
 H25C)
;
_shelx_res_checksum              73159
_shelx_hkl_checksum              49772
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'