Enantioselective synthesis of functionalized 1,4-dihydropyrazolo-[4',3':5,6]pyrano[2,3-<i>b</i>]quinolines through ferrocenyl-phosphine-catalyzed annulation of modified MBH carbonates and pyrazolones.
Xiao, Xiao; Shao, Bingxuan; Li, Jingyi; Yang, Zehui; Lu, Yin-Jie; Ling, Fei; Zhong, Weihui; Chemical communications (Cambridge, England) 57 (2021) 4690–4693; doi:10.1039/d1cc00989c

data_7128129
_publ_section_title
;
 Enantioselective synthesis of functionalized
 1,4-dihydropyrazolo-[4',3':5,6]pyrano[2,3-<i>b</i>]quinolines through
 ferrocenyl-phosphine-catalyzed annulation of modified MBH carbonates and
 pyrazolones.
;
_journal_issue                   38
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              4690
_journal_page_last               4693
_journal_paper_doi               10.1039/d1cc00989c
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         'C24 H19 N3 O3'
_chemical_formula_sum            'C24 H19 N3 O3'
_chemical_formula_weight         397.42
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-06-26
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-11-25 deposited with the CCDC.	2021-04-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.7277(5)
_cell_length_b                   12.2930(4)
_cell_length_c                   21.1373(7)
_cell_measurement_reflns_used    9152
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      72.07
_cell_measurement_theta_min      3.60
_cell_volume                     3826.9(2)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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      170.15
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.993
_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  0.0268
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            23639
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.067
_diffrn_reflns_theta_min         4.183
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.753
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6106
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1152 before and 0.0498 after correction.
The Ratio of minimum to maximum transmission is 0.8102.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_description       block
_exptl_crystal_F_000             1664
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3741
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0380
_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^)+(0.0462P)^2^+1.2918P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0979
_refine_ls_wR_factor_ref         0.0988
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3612
_reflns_number_total             3741
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc00989c2.cif
_cod_data_source_block           190625_zjut_kn_0m_pl
_cod_depositor_comments          'Adding full bibliography for 7128129.cif.'
_cod_database_code               7128129
_shelx_shelxl_version_number     2016/6
_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.a Ternary CH refined with riding coordinates:
 C12(H12)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C7(H7), C20(H20), C21(H21), C22(H22),
 C23(H23), C24(H24)
2.c X=CH2 refined with riding coordinates:
 C17(H17A,H17B)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C18(H18A,H18B,H18C)
;
_shelx_res_checksum              13258
_shelx_hkl_checksum              65826
_olex2_submission_special_instructions 'No special instructions were received'