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

data_1555834
_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 H6 O5'
_chemical_formula_sum            'C9 H6 O5'
_chemical_formula_weight         194.14
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yc'
_space_group_name_H-M_alt        'P 1 c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2015-05-06
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 91.943(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.26017(16)
_cell_length_b                   9.48057(19)
_cell_length_c                   11.4368(3)
_cell_measurement_reflns_used    4268
_cell_measurement_temperature    100.05(10)
_cell_measurement_theta_max      74.8930
_cell_measurement_theta_min      6.0090
_cell_volume                     786.75(3)
_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      100.05(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 4.1587
_diffrn_detector_type            Onyx
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details
;
  1 omega  -91.00   -8.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.9419  125.0000  -30.0000 83

  2 omega   78.00  119.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.9419  125.0000   90.0000 41

  3 omega   59.00  171.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000   15.0000   60.0000 112

  4 omega   89.00  178.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  111.0000 -120.0000 89

  5 omega  144.00  172.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  111.0000 -150.0000 28

  6 omega   82.00  168.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000   45.0000 -150.0000 86

  7 omega   81.00  129.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  111.0000 -150.0000 48

  8 omega   31.00   69.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -30.0000 -180.0000 38

  9 omega   27.00   61.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000 -111.0000 -120.0000 34

 10 omega   80.00  112.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000 -111.0000 -120.0000 32

 11 omega   69.00  106.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000 -111.0000 -180.0000 37

 12 omega   29.00   95.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000 -111.0000  -30.0000 66

 13 omega   79.00   92.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000 -111.0000    0.0000 13

 14 omega   65.00  105.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000 -118.0000   48.0000 40

 15 omega   45.00   75.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000 -111.0000    0.0000 30

 16 omega   29.00  107.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -94.0000   60.0000 78

 17 omega   39.00  127.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -61.0000  120.0000 88

 18 omega   31.00   57.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -30.0000   30.0000 26

 19 omega   34.00   76.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -45.0000  -30.0000 42

 20 omega   28.00   99.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000 -111.0000  -60.0000 71

 21 omega   29.00   61.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000 -111.0000 -180.0000 32

 22 omega -113.00  -16.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.9419  -57.0000  120.0000 97

 23 omega -119.00  -10.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.9419  -77.0000 -120.0000 109
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Onyx, Nova'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0894963000
_diffrn_orient_matrix_UB_12      -0.0059502000
_diffrn_orient_matrix_UB_13      0.1239961000
_diffrn_orient_matrix_UB_21      -0.0221946000
_diffrn_orient_matrix_UB_22      0.1609562000
_diffrn_orient_matrix_UB_23      0.0113872000
_diffrn_orient_matrix_UB_31      -0.1912862000
_diffrn_orient_matrix_UB_32      -0.0213953000
_diffrn_orient_matrix_UB_33      0.0515650000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0471
_diffrn_reflns_av_unetI/netI     0.0470
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6659
_diffrn_reflns_point_group_measured_fraction_full 0.742
_diffrn_reflns_point_group_measured_fraction_max 0.730
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.704
_diffrn_reflns_theta_min         4.664
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Nova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.186
_exptl_absorpt_correction_T_max  0.939
_exptl_absorpt_correction_T_min  0.875
_exptl_absorpt_correction_type   analytical
_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)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
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    1.639
_exptl_crystal_description       'rect. Prism'
_exptl_crystal_F_000             400
_exptl_crystal_recrystallization_method
'Crystals grown from ethylacetate/heptane'
_exptl_crystal_size_max          0.1455
_exptl_crystal_size_mid          0.0751
_exptl_crystal_size_min          0.0618
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.0(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         2356
_refine_ls_number_restraints     16
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0385
_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^)+(0.0613P)^2^+0.1326P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1005
_refine_ls_wR_factor_ref         0.1035
_reflns_Friedel_coverage         0.462
_reflns_Friedel_fraction_full    0.487
_reflns_Friedel_fraction_max     0.463
_reflns_number_gt                2227
_reflns_number_total             2356
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b02635_si_004.cif
_cod_data_source_block           cs2179
_cod_database_code               1555834
_chemical_oxdiff_formula         'C9 H6 O5'
_chemical_oxdiff_usercomment     'Laurent Bernad (Promega sample 48569)'
_reflns_odcompleteness_completeness 99.60
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2. Restrained distances
 O4-H4A = H10B-O10 = O9-H9A = H5B-O5 = O8A-H8A = O8B-H8B = O3-H3
 0.84 with sigma of 0.02
 O10-H4A = O4-H10B = H8A-O6_$2
 1.79 with sigma of 0.04
 O5-H9A = O9-H5B = H3-O1_$1
 1.83 with sigma of 0.04
 H8B-O4_$3
 2.5 with sigma of 0.04
3. Others
 Sof(O8B)=Sof(H8B)=Sof(H17A)=1-FVAR(1)
 Sof(O8A)=Sof(H8A)=Sof(H17)=FVAR(1)
 Sof(H5B)=Sof(H10B)=1-FVAR(2)
 Sof(H4A)=Sof(H9A)=FVAR(2)
4.a Ternary CH refined with riding coordinates:
 C8(H8), C17(H17), C17(H17A)
4.b Aromatic/amide H refined with riding coordinates:
 C3(H1), C5(H5), C6(H6), C12(H12), C14(H14), C15(H15)
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2015-04-29
_olex2_date_sample_submission    2015-04-28
_olex2_exptl_crystal_mounting_method 'Cryoloop with Krytox oil'
_olex2_submission_original_sample_id 'Promega 48569'
_olex2_submission_special_instructions 'No special instructions were received'