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

data_1555836
_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         'C8 H5 Cl O3'
_chemical_formula_sum            'C8 H5 Cl O3'
_chemical_formula_weight         184.57
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2015-06-30
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 101.170(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.8414(3)
_cell_length_b                   7.46056(17)
_cell_length_c                   15.3814(4)
_cell_measurement_reflns_used    4760
_cell_measurement_temperature    100.05(10)
_cell_measurement_theta_max      74.5220
_cell_measurement_theta_min      5.9020
_cell_volume                     1445.69(6)
_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      100.05(10)
_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 0.995
_diffrn_measurement_details
;
  1 omega  -69.00   31.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.9419   57.0000   60.0000 100

  2 omega -117.00  -12.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.9419  -37.0000 -150.0000 105

  3 omega  -71.00   34.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.9419   37.0000   30.0000 105

  4 omega  -98.00   -2.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.9419  125.0000   90.0000 96

  5 omega   59.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000   15.0000 -120.0000 119

  6 omega   27.00  115.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000 -111.0000  -90.0000 88

  7 omega   33.00   77.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -45.0000    0.0000 44

  8 omega   28.00  141.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -77.0000 -150.0000 113

  9 omega   33.00  136.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -61.0000 -150.0000 103

 10 omega   33.00  136.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -61.0000    0.0000 103

 11 omega   78.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000   61.0000  120.0000 100

 12 omega   30.00   69.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -30.0000 -120.0000 39

 13 omega   27.00  115.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000 -111.0000   30.0000 88

 14 omega   22.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -94.0000  150.0000 87

 15 omega   78.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000   61.0000   90.0000 100

 16 omega   73.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000   77.0000 -120.0000 105

 17 omega   22.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -94.0000 -180.0000 87

 18 omega   34.00   77.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -45.0000   90.0000 43

 19 omega   81.00  111.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000 -111.0000  150.0000 30

 20 omega   65.00  102.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000 -111.0000  120.0000 37

 21 omega  100.00  148.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  179.0000   90.0000 48

 22 omega   42.00   67.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -77.0000  -90.0000 25

 23 omega  105.00  140.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -77.0000  -90.0000 35

 24 omega   41.00   99.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  179.0000   90.0000 58
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Onyx, Nova'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0593481000
_diffrn_orient_matrix_UB_12      -0.0327099000
_diffrn_orient_matrix_UB_13      -0.0957225000
_diffrn_orient_matrix_UB_21      -0.0313304000
_diffrn_orient_matrix_UB_22      0.1993905000
_diffrn_orient_matrix_UB_23      -0.0084661000
_diffrn_orient_matrix_UB_31      0.1022452000
_diffrn_orient_matrix_UB_32      0.0420382000
_diffrn_orient_matrix_UB_33      -0.0345587000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0485
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8580
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.820
_diffrn_reflns_theta_min         5.864
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Nova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.358
_exptl_absorpt_correction_T_max  0.796
_exptl_absorpt_correction_T_min  0.568
_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    1.696
_exptl_crystal_description       prism
_exptl_crystal_F_000             752
_exptl_crystal_recrystallization_method 'heptane / ethyl acetate'
_exptl_crystal_size_max          0.2967
_exptl_crystal_size_mid          0.1561
_exptl_crystal_size_min          0.075
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.379
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     113
_refine_ls_number_reflns         1485
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0379
_refine_ls_R_factor_gt           0.0355
_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^)+(0.0454P)^2^+1.6915P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0870
_refine_ls_wR_factor_ref         0.0893
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1399
_reflns_number_total             1485
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b02635_si_009.cif
_cod_data_source_block           cs2195
_cod_original_cell_volume        1445.68(6)
_cod_database_code               1555836
_chemical_oxdiff_formula         'C8 H5 Cl O3'
_chemical_oxdiff_usercomment     'Laurent Bernad (Promega sample 49098)'
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6)
;
_shelx_res_checksum              45821
_shelx_hkl_checksum              73739
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2015-06-25
_olex2_date_sample_submission    2015-06-25
_olex2_exptl_crystal_mounting_method 'Nylon Cryoloop with Krytox'
_olex2_submission_original_sample_id 'Promega 49098'
_olex2_submission_special_instructions 'No special instructions were received'