Efficient synthesis of diethyl benzo[c]cinoline-3,8-dicarboxylate for fluorescence quenching materials
Wang, Ning; Yang, Jin-Chuang; Chen, Li-Dong; Li, Jia; An, Yue; Lü, Cheng-Wei; Tian, Yun-Qi; New J. Chem. 41 (2017) 2786–; doi:10.1039/C6NJ03989H

data_7056030
_publ_section_title
;
 Efficient synthesis of diethyl benzo[c]cinoline-3,8-dicarboxylate for
 fluorescence quenching materials
;
_journal_issue                   7
_journal_name_full               'New J. Chem.'
_journal_page_first              2786
_journal_paper_doi               10.1039/C6NJ03989H
_journal_volume                  41
_journal_year                    2017
_chemical_formula_moiety         'C18 H16 N2 O5'
_chemical_formula_sum            'C18 H16 N2 O5'
_chemical_formula_weight         340.33
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-10-08
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_audit_update_record
;
2016-10-09 deposited with the CCDC.
2017-02-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.2607(15)
_cell_length_b                   14.168(3)
_cell_length_c                   27.700(5)
_cell_measurement_reflns_used    2761
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      24.485
_cell_measurement_theta_min      2.854
_cell_volume                     3241.9(11)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'CCD Area Detector'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0532
_diffrn_reflns_av_unetI/netI     0.0424
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            19537
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.251
_diffrn_reflns_theta_min         1.470
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6318
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1004 before and 0.0471 after correction.
The Ratio of minimum to maximum transmission is 0.8473.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_description       block
_exptl_crystal_F_000             1424
_refine_diff_density_max         0.386
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       0.0020(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3964
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.1385
_refine_ls_R_factor_gt           0.0651
_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^)+(0.0683P)^2^+1.8323P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1498
_refine_ls_wR_factor_ref         0.1885
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2039
_reflns_number_total             3964
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6nj03989h2.cif
_cod_data_source_block           20151229l_0m
_cod_depositor_comments
'Adding full bibliography for 7056029--7056030.cif.'
_cod_database_code               7056030
_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
2. Others
 Sof(O5A)=1-FVAR(1)
 Sof(O5)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C19(H19A,H19B)
3.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C12(H12), C13(H13), C16(H16), C0AA(H0AA), C17(H17)
3.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C20(H20A,H20B,H20C)
;
_shelx_res_checksum              2891
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'