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

data_1555833
_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         'C22 H21 N O5'
_chemical_formula_sum            'C22 H21 N O5'
_chemical_formula_weight         379.40
_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             2015-10-16
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                84.150(4)
_cell_angle_beta                 72.472(4)
_cell_angle_gamma                64.512(5)
_cell_formula_units_Z            2
_cell_length_a                   8.5998(3)
_cell_length_b                   9.2091(5)
_cell_length_c                   13.2372(7)
_cell_measurement_reflns_used    7291
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      32.0340
_cell_measurement_theta_min      4.3440
_cell_volume                     901.91(9)
_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, 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 0.995
_diffrn_measured_fraction_theta_max 0.924
_diffrn_measurement_details
;
  1 omega  -49.00   38.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -29.5315   57.0000   90.0000 87

  2 omega  -55.00   -6.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -29.5315  -57.0000  -60.0000 49

  3 omega  -41.00   -8.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -29.5315  -77.0000    0.0000 33

  4 omega  -25.00    6.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -29.5315  -82.0000  115.9773 31

  5 omega  -80.00    4.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -29.5315  -77.0000   60.0000 84

  6 omega  -90.00    4.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -29.5315  -77.0000 -120.0000 94

  7 omega  -96.00   37.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -29.5315   19.0000  -30.0000 133

  8 omega  -63.00   32.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -29.5315   77.0000    0.0000 95

  9 omega  -78.00    8.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -29.5315  106.0000  132.0000 86

 10 omega -102.00    2.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -29.5315  -38.0000  120.0000 104

 11 omega -100.00  -65.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -29.5315  -57.0000  -60.0000 35

 12 omega  -99.00  -68.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -29.5315  -77.0000    0.0000 31

 13 omega -109.00  -75.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -29.5315 -178.0000  150.0000 34
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0021190000
_diffrn_orient_matrix_UB_12      0.0781786000
_diffrn_orient_matrix_UB_13      -0.0065220000
_diffrn_orient_matrix_UB_21      0.0035422000
_diffrn_orient_matrix_UB_22      -0.0032832000
_diffrn_orient_matrix_UB_23      -0.0539902000
_diffrn_orient_matrix_UB_31      -0.0952811000
_diffrn_orient_matrix_UB_32      0.0341373000
_diffrn_orient_matrix_UB_33      0.0142631000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_av_unetI/netI     0.0386
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.924
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            19206
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.924
_diffrn_reflns_theta_full        31.000
_diffrn_reflns_theta_max         32.479
_diffrn_reflns_theta_min         3.570
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94978
_exptl_absorpt_correction_type   multi-scan
_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)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_description
;
;
_exptl_crystal_F_000             400
_exptl_crystal_recrystallization_method 'Crystallized from CH2Cl2 / CH3OH'
_exptl_crystal_size_max          0.5224
_exptl_crystal_size_mid          0.3238
_exptl_crystal_size_min          0.213
_refine_diff_density_max         0.473
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         6013
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0493
_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^)+(0.0618P)^2^+0.2313P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1212
_refine_ls_wR_factor_ref         0.1300
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4862
_reflns_number_total             6013
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b02635_si_005.cif
_cod_data_source_block           cs2249
_cod_original_cell_volume        901.91(8)
_cod_database_code               1555833
_chemical_oxdiff_formula         'C22 H21 N O5'
_chemical_oxdiff_usercomment     'Laurent Bernad (Promega 052-0350)'
_reflns_odcompleteness_completeness 99.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B), C20(H20A,
 H20B), C21(H21A,H21B), C22(H22A,H22B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C15(H15)
;
_shelx_res_checksum              61642
_shelx_hkl_checksum              15343
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2015-10-15
_olex2_date_sample_submission    2015-10-14
_olex2_exptl_crystal_mounting_method 'Mounted on nylon loop with Krytox'
_olex2_submission_original_sample_id 'Promega O52-0350'
_olex2_submission_special_instructions 'No special instructions were received'