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

data_1555835
_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         'C9 H5 O5, C6 H16 N'
_chemical_formula_sum            'C15 H21 N O5'
_chemical_formula_weight         295.33
_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             2015-04-02
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                96.026(3)
_cell_angle_beta                 90.185(2)
_cell_angle_gamma                110.137(3)
_cell_formula_units_Z            2
_cell_length_a                   8.8765(3)
_cell_length_b                   9.1065(3)
_cell_length_c                   9.7523(3)
_cell_measurement_reflns_used    9136
_cell_measurement_temperature    100.00(14)
_cell_measurement_theta_max      74.7390
_cell_measurement_theta_min      4.5230
_cell_volume                     735.38(4)
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(14)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 4.1587
_diffrn_detector_type            Onyx
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details
;
  1 omega   15.00   48.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.9419   57.0000   60.0000 33

  2 omega   55.00  114.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.9419   57.0000   60.0000 59

  3 omega   83.00  133.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   77.0000   82.3759 50

  4 omega  110.00  148.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       74.0000   75.0000  124.1242 38

  5 omega  132.00  169.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000   77.0000   30.0000 37

  6 omega  115.00  165.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000   77.0000    0.0000 50

  7 omega  129.00  177.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000   77.0000  -90.0000 48

  8 omega  153.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000   77.0000 -180.0000 25

  9 omega  135.00  173.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000   45.0000 -180.0000 38

 10 omega  124.00  177.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000   77.0000 -150.0000 53

 11 omega  102.00  149.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   77.0000  -95.8550 47

 12 omega   83.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   77.0000  -15.2384 26

 13 omega   73.00  154.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000   77.0000   60.0000 81

 14 omega  116.00  142.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000   61.0000   30.0000 26

 15 omega   87.00  172.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000   45.0000  120.0000 85

 16 omega   81.00  125.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -61.0000   90.0000 44

 17 omega   79.00  112.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000 -111.0000   30.0000 33

 18 omega   59.00   92.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -94.0000  -30.0000 33

 19 omega   58.00  101.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -94.0000   30.0000 43

 20 omega   62.00   92.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -94.0000   60.0000 30

 21 omega   59.00  106.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -94.0000  120.0000 47

 22 omega   59.00  112.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000 -111.0000  120.0000 53

 23 omega   37.00   66.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -61.0000   90.0000 29

 24 omega   35.00   69.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -30.0000   60.0000 34

 25 omega   34.00   77.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -45.0000    0.0000 43

 26 omega   33.00   65.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -45.0000  -60.0000 32

 27 omega   24.00   50.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -94.0000  -30.0000 26

 28 omega   28.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000 -111.0000  -30.0000 81

 29 omega   78.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -94.0000 -120.0000 27

 30 omega   82.00  112.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000 -111.0000 -120.0000 30

 31 omega   71.00   96.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -94.0000 -180.0000 25

 32 omega   34.00   70.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -94.0000 -120.0000 36

 33 omega   30.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -94.0000 -180.0000 33

 34 omega   27.00   66.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000 -111.0000 -120.0000 39

 35 omega   34.00   76.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000 -111.0000   30.0000 42

 36 omega   14.00   54.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.9419   37.0000 -120.0000 40

 37 omega   56.00  117.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.9419   37.0000 -120.0000 61

 38 omega   61.00   86.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   75.0000  -98.1801 25

 39 omega   51.00   77.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       82.0000   70.0000  -22.9975 26

 40 omega   74.00  116.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000   77.0000   30.0000 42

 41 omega   74.00  100.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000   77.0000   90.0000 26

 42 omega   73.00  139.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000   77.0000  120.0000 66

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

 44 omega   71.00   96.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      102.0000   76.0000  109.5112 25

 45 omega   75.00  165.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000   77.0000  150.0000 90

 46 omega   80.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000   61.0000   30.0000 28

 47 omega   73.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000   77.0000    0.0000 30

 48 omega   76.00  142.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000   77.0000  -30.0000 66

 49 omega   81.00  146.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000   61.0000  -90.0000 65

 50 omega   79.00  141.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000   61.0000 -150.0000 62

 51 omega   81.00  158.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000   61.0000 -120.0000 77

 52 omega   73.00  120.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000   77.0000 -180.0000 47

 53 omega   74.00  120.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000   77.0000  -90.0000 46

 54 omega   73.00  153.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000   77.0000  -60.0000 80

 55 omega   74.00  100.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000   77.0000 -120.0000 26

 56 omega   73.00   99.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000   77.0000 -150.0000 26

 57 omega   33.00   59.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   76.0000 -173.6354 26

 58 omega   38.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   76.0000 -156.4792 25

 59 omega   30.00   56.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   75.0000  -98.1801 26

 60 omega   36.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   77.0000  -95.8550 55

 61 omega   30.00   61.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   77.0000   15.3146 31

 62 omega   37.00   79.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   76.0000   53.2473 42

 63 omega   41.00   67.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       74.0000   75.0000  124.1242 26

 64 omega   37.00   68.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   75.0000  152.7798 31

 65 omega   31.00   61.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   77.0000   82.3759 30

 66 omega   20.00   46.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   80.0000  110.0076 26

 67 omega   19.00   44.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   80.0000   58.8798 25

 68 omega   12.00   66.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.9419   37.0000    0.0000 54

 69 omega   29.00   55.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   77.0000  -15.2384 26

 70 omega   19.00   44.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   82.0000  -58.6762 25

 71 omega   19.00   44.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   81.0000 -108.3905 25

 72 omega   10.00   35.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       46.0000   84.0000   -1.8887 25

 73 omega   -2.00   23.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       38.0000   93.0000  131.8201 25

 74 omega   14.00   39.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   83.0000  153.8480 25

 75 omega   65.00  129.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  179.0000    0.0000 64

 76 omega  -73.00    2.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.9419   77.0000 -120.0000 75

 77 omega  -96.00   -5.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.9419  125.0000    0.0000 91
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Onyx, Nova'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.1026582000
_diffrn_orient_matrix_UB_12      -0.1736403000
_diffrn_orient_matrix_UB_13      0.0084694000
_diffrn_orient_matrix_UB_21      0.0248869000
_diffrn_orient_matrix_UB_22      -0.0394569000
_diffrn_orient_matrix_UB_23      -0.1538730000
_diffrn_orient_matrix_UB_31      0.1519033000
_diffrn_orient_matrix_UB_32      -0.0343411000
_diffrn_orient_matrix_UB_33      0.0390975000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0448
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            15919
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.093
_diffrn_reflns_theta_min         4.563
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Nova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.831
_exptl_absorpt_correction_T_max  0.941
_exptl_absorpt_correction_T_min  0.899
_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    1.334
_exptl_crystal_description       plate
_exptl_crystal_F_000             316
_exptl_crystal_recrystallization_method 'Crystallized from water'
_exptl_crystal_size_max          0.1996
_exptl_crystal_size_mid          0.1151
_exptl_crystal_size_min          0.0982
_refine_diff_density_max         0.404
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3011
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0381
_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^)+(0.0612P)^2^+0.1956P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1021
_refine_ls_wR_factor_ref         0.1070
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2670
_reflns_number_total             3011
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b02635_si_003.cif
_cod_data_source_block           cs2177
_cod_database_code               1555835
_chemical_oxdiff_formula         'C15 H21 N O5'
_chemical_oxdiff_usercomment
'Laurent Bernad (Promega Biosciences) Sample 48330'
_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:
 C10(H10A,H10B), C12(H12A,H12B), C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C6(H6), C8(H8)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C13(H13A,H13B,H13C), C15(H15A,H15B,H15C)
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2015-04-01
_olex2_date_sample_submission    2015-03-31
_olex2_exptl_crystal_mounting_method 'The large plate was cut into a prism.'
_olex2_submission_original_sample_id 'Promega Biosciences 48330'
_olex2_submission_special_instructions 'No special instructions were received'