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

data_1555837
_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         'C35 H34 N2 O5'
_chemical_formula_sum            'C35 H34 N2 O5'
_chemical_formula_weight         562.64
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2016-02-04
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                90
_cell_angle_beta                 90.3246(17)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.36155(18)
_cell_length_b                   12.6426(2)
_cell_length_c                   22.9131(5)
_cell_measurement_reflns_used    8705
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      71.9310
_cell_measurement_theta_min      5.0620
_cell_volume                     2711.82(9)
_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, 2008)'
_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 0.996
_diffrn_measured_fraction_theta_max 0.982
_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    -20.00  19.00   1.00    1.00    --    0.00 -57.00-180.00   39
  2  \w     32.00  77.00   1.00    1.00    --    0.00-178.00  90.00   45
  3  \w    -68.00 -23.00   1.00    1.00    --    0.00 -57.00-180.00   45
  4  \w   -112.00 -18.00   1.00    6.00    --  -55.00 125.00 -90.00   94
  5  \w     76.00 126.00   1.00    6.00    --   55.00 125.00 -30.00   50
  6  \w     28.00 114.00   1.00    6.00    --   55.00  77.00 150.00   86
  7  \w    -16.00  42.00   1.00    6.00    --   55.00 -99.00 -90.00   58
  8  \w      3.00  80.00   1.00    6.00    --   55.00 -38.00 -30.00   77
  9  \w     52.00  77.00   1.00    6.00    --   55.00-125.00 120.00   25
 10  \w     77.00 108.00   1.00    6.00    --   55.00 125.00  60.00   31
 11  \w     38.00 121.00   1.00    6.00    --   55.00  57.00 120.00   83
 12  \w     -2.00  24.00   1.00    6.00    --   55.00-125.00 120.00   26
 13  \w     82.00 100.00   1.00   20.00    --  110.00 -92.00 -30.00   18
 14  \w    118.00 169.00   1.00   20.00    --  110.00  25.00 -90.00   51
 15  \w     45.00 130.00   1.00   20.00    --  110.00 -64.00  90.00   85
 16  \w     41.00  67.00   1.00   20.00    --  110.00 -92.00-120.00   26
 17  \w     76.00 115.00   1.00   20.00    --  110.00  25.00 -90.00   39
 18  \w    132.00 178.00   1.00   20.00    --  110.00  38.00 120.00   46
 19  \w     38.00 133.00   1.00   20.00    --  110.00 -38.00-150.00   95
 20  \w     85.00 111.00   1.00   20.00    --  110.00  38.00 120.00   26
 21  \w     93.00 119.00   1.00   20.00    --  110.00 -92.00  30.00   26
 22  \w     46.00  72.00   1.00   20.00    --  110.00 -92.00  30.00   26
 23  \w     67.00 105.00   1.00   20.00    --  110.00 -92.00 150.00   38
 24  \w     41.00 143.00   1.00   20.00    --  110.00 -25.00  60.00  102
 25  \w     82.00  98.00   1.00   20.00    --  110.00 -92.00-120.00   16
 26  \w     45.00  70.00   1.00   20.00    --  110.00 -92.00 -30.00   25
 27  \w     37.00 129.00   1.00   20.00    --  110.00 -25.00 -60.00   92
 28  \w     38.00  64.00   1.00   20.00    --  110.00 -87.00  71.00   26
 29  \w     77.00 103.00   1.00   20.00    --  110.00  87.00-171.00   26
 30  \w     32.00  77.00   1.00    1.00    --    0.00-178.00 -90.00   45
 31  \w    -36.00  18.00   1.00    1.00    --    0.00  87.00-171.00   54
 32  \w     52.00  99.00   1.00    6.00    --   55.00  57.00-150.00   47
 33  \w     95.00 126.00   1.00    6.00    --   55.00 125.00-150.00   31
 34  \w     80.00 131.00   1.00   20.00    --  110.00  77.00-180.00   51
 35  \w     96.00 122.00   1.00   20.00    --  110.00  64.00-120.00   26
 36  \w     88.00 113.00   1.00   20.00    --  110.00  50.00 150.00   25
 37  \w    102.00 147.00   1.00   20.00    --  110.00  38.00   0.00   45
 38  \w     80.00 132.00   1.00   20.00    --  110.00  77.00 150.00   52
 39  \w     92.00 118.00   1.00   20.00    --  110.00  64.00 -90.00   26
 40  \w    145.00 176.00   1.00   20.00    --  110.00  64.00-120.00   31
;
_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      0.0598570000
_diffrn_orient_matrix_UB_12      0.0887451000
_diffrn_orient_matrix_UB_13      -0.0389253000
_diffrn_orient_matrix_UB_21      0.1158282000
_diffrn_orient_matrix_UB_22      0.0235723000
_diffrn_orient_matrix_UB_23      0.0462231000
_diffrn_orient_matrix_UB_31      0.1003683000
_diffrn_orient_matrix_UB_32      -0.0800959000
_diffrn_orient_matrix_UB_33      -0.0295130000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0401
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            21502
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        68.000
_diffrn_reflns_theta_max         72.036
_diffrn_reflns_theta_min         3.858
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.743
_exptl_absorpt_correction_T_max  0.961
_exptl_absorpt_correction_T_min  0.903
_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            'dark violet'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_description       plate
_exptl_crystal_F_000             1192
_exptl_crystal_preparation
'Crystal looks dark transparent red in transmitted light, opaque purple in reflected light.'
_exptl_crystal_recrystallization_method
;
Crystallized from CH2Cl2/CH3OH.
Crystals look dark red in transmitted light.
;
_exptl_crystal_size_max          0.184
_exptl_crystal_size_mid          0.134
_exptl_crystal_size_min          0.055
_refine_diff_density_max         0.395
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     383
_refine_ls_number_reflns         5256
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0411
_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^)+(0.0481P)^2^+1.1876P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1016
_refine_ls_wR_factor_ref         0.1077
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4514
_reflns_number_total             5256
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b02635_si_002.cif
_cod_data_source_block           cs2271
_cod_database_code               1555837
_chemical_oxdiff_formula         'C35 H34 N2 O5'
_chemical_oxdiff_usercomment     'Laruent Bernad (Promega sample sjd-0399)'
_reflns_odcompleteness_completeness 99.55
_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
2.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), C26(H26A,H26B), C27(H27A,H27B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C9(H9), C30(H30), C31(H31), C33(H33)
;
_shelx_res_checksum              92543
_shelx_hkl_checksum              26181
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2016-02-01
_olex2_date_sample_submission    2016-01-28
_olex2_exptl_crystal_mounting_method 'Nylon cryloop with Krytox oil.'
_olex2_submission_original_sample_id SJD-0399
_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 1.806
_oxdiff_exptl_absorpt_empirical_full_min 0.737