Novel 7-(1H-pyrrol-1-yl)spiro[chromeno[4,3-b]quinoline-6,1′-cycloalkanes]: synthesis, cross-coupling reactions, and photophysical properties
Silva, Letícia B.; Stefanello, Felipe S.; Feitosa, Sarah C.; Frizzo, Clarissa P.; Martins, Marcos A. P.; Zanatta, Nilo; Iglesias, Bernardo A.; Bonacorso, Helio G.; New Journal of Chemistry 45 (2021) 4061–4070; doi:10.1039/D0NJ05740A

data_7060381
_publ_section_title
;
 Novel
 7-(1H-pyrrol-1-yl)spiro[chromeno[4,3-b]quinoline-6,1&#x2032;-cycloalkanes]:
 synthesis, cross-coupling reactions, and photophysical properties
;
_journal_issue                   8
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              4061
_journal_page_last               4070
_journal_paper_doi               10.1039/D0NJ05740A
_journal_volume                  45
_journal_year                    2021
_chemical_formula_moiety         'C26 H24 N2 O'
_chemical_formula_sum            'C26 H24 N2 O'
_chemical_formula_weight         380.47
_chemical_name_common            spiroquinoline
_chemical_name_systematic
;
'7-(1H-pyrrol-1-yl)spiro[chromeno[4,3-b]quinoline-6,1'-cycloheptane]'
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2020-10-14
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_audit_update_record
;
2020-10-15 deposited with the CCDC.	2021-01-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.0660(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.6841(4)
_cell_length_b                   13.1101(3)
_cell_length_c                   20.4047(5)
_cell_measurement_reflns_used    9964
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      72.323
_cell_measurement_theta_min      5.362
_cell_volume                     4031.75(17)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'BRUKER APEX-III'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXL97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean none
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_unetI/netI     0.0172
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            37221
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.657
_diffrn_reflns_theta_min         5.362
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.596
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6451
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0794 before and 0.0532 after correction.
The Ratio of minimum to maximum transmission is 0.8560.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1616
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.510
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.032
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3964
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0641
_refine_ls_R_factor_gt           0.0533
_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^)+(0.0819P)^2^+1.8562P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1496
_refine_ls_wR_factor_ref         0.1592
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3235
_reflns_number_total             3964
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0nj05740a2.cif
_cod_data_source_block           mmq0104_0m-auto
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'none' was changed to
'?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7060381.cif.
;
_cod_database_code               7060381
_shelx_shelxl_version_number     2018/3
_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:
 C61(H61A,H61B), C62(H62A,H62B), C63(H63A,H63B), C64(H64A,H64B), C65(H65A,
 H65B), C66(H66A,H66B)
2.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C9(H9), C8(H8), C3(H3), C2(H2), C1(H1), C11(H11), C72(H72),
 C73(H73), C74(H74), C75(H75), C4(H4)
;
_shelx_res_checksum              65033
_shelx_hkl_checksum              86910
_olex2_submission_special_instructions 'No special instructions were received'