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

data_1555839
_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         'C21 H20 Cl N O3'
_chemical_formula_sum            'C21 H20 Cl N O3'
_chemical_formula_weight         369.83
_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   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2015-07-20
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                108.425(11)
_cell_angle_beta                 106.740(10)
_cell_angle_gamma                90.498(9)
_cell_formula_units_Z            2
_cell_length_a                   8.3659(8)
_cell_length_b                   8.5097(10)
_cell_length_c                   13.3207(17)
_cell_measurement_reflns_used    917
_cell_measurement_temperature    99.95(10)
_cell_measurement_theta_max      24.4740
_cell_measurement_theta_min      3.7940
_cell_volume                     856.37(19)
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.95(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 0.996
_diffrn_measurement_details
;
  1 omega  -60.00   38.00   1.0000   42.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.0820   89.0000  114.0000 98

  2 omega  -92.00   13.00   1.0000   42.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.0820  -77.0000    0.0000 105

  3 omega  -44.00   50.00   1.0000   42.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.0820   57.0000  -90.0000 94

  4 omega  -55.00   13.00   1.0000   42.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.0820  -77.0000 -120.0000 68

  5 omega  -44.00   50.00   1.0000   42.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.0820   57.0000 -120.0000 94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0373375000
_diffrn_orient_matrix_UB_12      0.0756736000
_diffrn_orient_matrix_UB_13      0.0073230000
_diffrn_orient_matrix_UB_21      -0.0247268000
_diffrn_orient_matrix_UB_22      -0.0118686000
_diffrn_orient_matrix_UB_23      0.0439829000
_diffrn_orient_matrix_UB_31      0.0769992000
_diffrn_orient_matrix_UB_32      0.0441069000
_diffrn_orient_matrix_UB_33      0.0385813000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0896
_diffrn_reflns_av_unetI/netI     0.1546
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6494
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.614
_diffrn_reflns_theta_min         3.565
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.245
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_correction_T_min  0.971
_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    1.434
_exptl_crystal_description       plank
_exptl_crystal_F_000             388
_exptl_crystal_recrystallization_method
'Crystallized from heptane / ethyl acetate'
_exptl_crystal_size_max          0.2106
_exptl_crystal_size_mid          0.095
_exptl_crystal_size_min          0.0308
_refine_diff_density_max         0.424
_refine_diff_density_min         -0.367
_refine_diff_density_rms         0.089
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3219
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.103
_refine_ls_R_factor_all          0.1500
_refine_ls_R_factor_gt           0.0905
_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^)+(0.0332P)^2^+0.6071P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1475
_refine_ls_wR_factor_ref         0.1691
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2001
_reflns_number_total             3219
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b02635_si_010.cif
_cod_data_source_block           cs2209
_cod_original_cell_volume        856.36(18)
_cod_database_code               1555839
_chemical_oxdiff_formula         'C21 H20 Cl N O3'
_chemical_oxdiff_usercomment     'Laurent Bernad (Promega sample 49230)'
_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:
 C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,
 H16B), C17(H17A,H17B), C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3A), C4(H4), C6(H6), C20(H20)
2.d Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_shelx_res_checksum              20405
_shelx_hkl_checksum              93824
_shelx_shelxl_version_number     2014/7
_olex2_exptl_crystal_mounting_method 'Mounted on Nylon Cryoloop with Krytox oil'
_olex2_submission_original_sample_id 'Promega 49230'
_olex2_submission_special_instructions 'No special instructions were received'