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

data_1555840
_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         'C33 H30 N2 O5, H2 O, 2(C H4 O)'
_chemical_formula_sum            'C35 H40 N2 O8'
_chemical_formula_weight         616.69
_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
_audit_creation_date             2016-01-05
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                96.799(5)
_cell_angle_beta                 105.982(4)
_cell_angle_gamma                92.907(4)
_cell_formula_units_Z            2
_cell_length_a                   9.6296(4)
_cell_length_b                   11.8041(7)
_cell_length_c                   14.0277(8)
_cell_measurement_reflns_used    4932
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      71.8380
_cell_measurement_theta_min      3.7690
_cell_volume                     1516.29(14)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0061
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -25.00  42.00   1.00    1.00    --    0.00 -99.00   0.00   67
  2  \w    -28.00  69.00   1.00    1.00    --    0.00  73.00 133.00   97
  3  \w    -85.00  15.00   1.00    1.50    --  -55.00  77.00   0.00  100
  4  \w   -112.00 -18.00   1.00    1.50    --  -55.00 125.00  90.00   94
  5  \w     34.00 124.00   1.00    1.50    --   55.00  57.00 -30.00   90
  6  \w    -14.00  75.00   1.00    1.50    --   55.00 -57.00  30.00   89
  7  \w    -14.00  75.00   1.00    1.50    --   55.00 -57.00-180.00   89
  8  \w     29.00 127.00   1.00    1.50    --   55.00  38.00 -60.00   98
  9  \w     73.00 126.00   1.00    1.50    --   55.00 125.00 150.00   53
 10  \w     40.00 132.00   1.00    6.00    --  110.00 -50.00 -60.00   92
 11  \w     38.00 148.00   1.00    6.00    --  110.00 -92.00-180.00  110
 12  \w     38.00 136.00   1.00    6.00    --  110.00 -38.00   0.00   98
 13  \w     38.00 148.00   1.00    6.00    --  110.00 -92.00  90.00  110
 14  \w     80.00 178.00   1.00    6.00    --  110.00  77.00 -60.00   98
 15  \w     87.00 177.00   1.00    6.00    --  110.00  64.00 -90.00   90
 16  \w     40.00 132.00   1.00    6.00    --  110.00 -50.00-120.00   92
 17  \w     38.00  90.00   1.00    6.00    --  110.00-111.00-180.00   52
 18  \w     87.00 177.00   1.00    6.00    --  110.00  64.00   0.00   90
 19  \w     40.00 132.00   1.00    6.00    --  110.00 -50.00 150.00   92
 20  \w     37.00 178.00   1.00    6.00    --  110.00   0.00  90.00  141
 21  \w     38.00 149.00   1.00    6.00    --  110.00 -93.00 -41.90  111
 22  \w    -25.00  42.00   1.00    1.00    --    0.00 -99.00 150.00   67
 23  \w    -30.00  70.00   1.00    1.00    --    0.00  77.00 -30.00  100
 24  \w   -124.00 -34.00   1.00    1.50    --  -55.00 -57.00 150.00   90
 25  \w     34.00 124.00   1.00    1.50    --   55.00  57.00-150.00   90
 26  \w     25.00 125.00   1.00    1.50    --   55.00  77.00   0.00  100
 27  \w     25.00 125.00   1.00    1.50    --   55.00  77.00 120.00  100
 28  \w     25.00 125.00   1.00    1.50    --   55.00  77.00-120.00  100
 29  \w     25.00 125.00   1.00    1.50    --   55.00  77.00  60.00  100
 30  \w     84.00 178.00   1.00    6.00    --  110.00  38.00  90.00   94
 31  \w     80.00 178.00   1.00    6.00    --  110.00  77.00-180.00   98
 32  \w     80.00 178.00   1.00    6.00    --  110.00  77.00  30.00   98
 33  \w     84.00 178.00   1.00    6.00    --  110.00  38.00 120.00   94
 34  \w     84.00 178.00   1.00    6.00    --  110.00  38.00-120.00   94
 35  \w     80.00 178.00   1.00    6.00    --  110.00  77.00 -30.00   98
 36  \w     76.00 178.00   1.00    6.00    --  110.00  25.00-180.00  102
 37  \w     80.00 131.00   1.00    6.00    --  110.00  77.00-120.00   51
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0602020000
_diffrn_orient_matrix_UB_12      0.1118262000
_diffrn_orient_matrix_UB_13      -0.0334636000
_diffrn_orient_matrix_UB_21      -0.1179022000
_diffrn_orient_matrix_UB_22      -0.0699021000
_diffrn_orient_matrix_UB_23      -0.0874623000
_diffrn_orient_matrix_UB_31      -0.1018872000
_diffrn_orient_matrix_UB_32      -0.0040663000
_diffrn_orient_matrix_UB_33      0.0673334000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0466
_diffrn_reflns_av_unetI/netI     0.0523
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            21336
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.500
_diffrn_reflns_theta_max         72.116
_diffrn_reflns_theta_min         3.786
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.785
_exptl_absorpt_correction_T_max  0.928
_exptl_absorpt_correction_T_min  0.881
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
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            violet
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_description       prism
_exptl_crystal_F_000             656
_exptl_crystal_recrystallization_method
'Slow evaporation of a CH3OH/CH2Cl2 mixture.'
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.177
_exptl_crystal_size_min          0.107
_refine_diff_density_max         0.478
_refine_diff_density_min         -0.427
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     430
_refine_ls_number_reflns         5789
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0924
_refine_ls_R_factor_gt           0.0610
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0791P)^2^+0.8137P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1563
_refine_ls_wR_factor_ref         0.1772
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4143
_reflns_number_total             5789
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b02635_si_007.cif
_cod_data_source_block           cs2261
_cod_original_cell_volume        1516.28(14)
_cod_database_code               1555840
_chemical_oxdiff_formula         'C33 H30 N2 O5 C2 H8 O2 H2 O'
_chemical_oxdiff_usercomment     'Promega 49775 (Carla recrystallization)'
_reflns_odcompleteness_completeness 98.78
_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 C(H,H,H) groups, All C(H,H,H,H,H,H) groups, All O(H) groups, All O(H,H)
  groups
2. Others
 Sof(O8B)=Sof(H8B)=Sof(H36D)=Sof(H36E)=Sof(H36F)=1-FVAR(1)
 Sof(O8A)=Sof(H8A)=Sof(H36A)=Sof(H36B)=Sof(H36C)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B), C18(H18A,
 H18B), C19(H19A,H19B), C20(H20A,H20B), C21(H21A,H21B), C22(H22A,H22B),
 C23(H23A,H23B), C24(H24A,H24B), C25(H25A,H25B)
3.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C9(H9), C28(H28), C29(H29), C31(H31)
3.c Idealised Me refined as rotating group:
 C34(H34A,H34B,H34C), C36(H36A,H36B,H36C), C36(H36D,H36E,H36F)
3.d Idealised tetrahedral OH refined as rotating group:
 O7(H7), O8A(H8A), O8B(H8B)
;
_shelx_res_checksum              44419
_shelx_hkl_checksum              38521
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2016-01-04
_olex2_date_sample_submission    2015-09-15
_olex2_exptl_crystal_mounting_method 'Nylon cryoloop with Krytox oil'
_olex2_submission_original_sample_id 'Promega 49775'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.565
_oxdiff_exptl_absorpt_empirical_full_min 0.773