Synthesis and Fluorosolvatochromic Properties of 1,7-Annulated Indoles
Giardinetti, Maxime; Marrot, Jérome; Coeffard, Vincent; Moreau, Xavier; Greck, Christine; New J. Chem. 41 (2017) 7331–7338; doi:10.1039/C7NJ00365J

data_7056302
_publ_section_title
;
 Synthesis and Fluorosolvatochromic Properties of 1,7-Annulated Indoles
;
_journal_issue                   15
_journal_name_full               'New J. Chem.'
_journal_page_first              7331
_journal_page_last               7338
_journal_paper_doi               10.1039/C7NJ00365J
_journal_volume                  41
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_sum            'C23 H13 Cl N4'
_chemical_formula_weight         380.82
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-01-18 deposited with the CCDC.
2017-06-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 117.346(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.9521(8)
_cell_length_b                   10.5005(5)
_cell_length_c                   14.1217(8)
_cell_measurement_reflns_used    9936
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.58
_cell_measurement_theta_min      2.53
_cell_volume                     1837.69(18)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1256
_diffrn_reflns_av_unetI/netI     0.0479
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            86494
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.033
_diffrn_reflns_theta_max         25.033
_diffrn_reflns_theta_min         2.530
_diffrn_source                   microsource
_exptl_absorpt_coefficient_mu    0.224
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, V2014/5)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_description       platelet
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.020
_exptl_transmission_factor_max   0.7452
_exptl_transmission_factor_min   0.5449
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details
; 
 Flack x determined using 2032 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.03(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     505
_refine_ls_number_reflns         6476
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.113
_refine_ls_R_factor_all          0.0797
_refine_ls_R_factor_gt           0.0530
_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^)+(0.0604P)^2^+0.6695P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1221
_refine_ls_wR_factor_ref         0.1402
_reflns_Friedel_coverage         0.887
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                5069
_reflns_number_total             6476
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7nj00365j2.cif
_cod_data_source_block           mg2141_a
_cod_original_cell_volume        1837.68(18)
_cod_database_code               7056302
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.936
_shelx_estimated_absorpt_t_max   0.996
_exptl_absorpt_special_details   'Blessing, Acta Cryst. (1995) A51, 33-38'
_shelx_res_checksum              45563