Crystal engineering of molecules with through-space α-effect hydrogen bonds: 3a,6:7,9a-diepoxybenzo[de]isoquinolines possessing a free amino group
Antonova, Alexandra S.; Nikitina, Eugeniya V.; Valchuk, karine S.; Grigoriev , Mikhail; Gomila, Rosa Maria; Frontera, Antonio; Zubkov, Fedor Ivanovich; CrystEngComm  (2022) –; doi:10.1039/D2CE00903J

data_7245296
_publ_section_title
;
 Crystal engineering of molecules with through-space \a-effect hydrogen
 bonds: 3a,6:7,9a-diepoxybenzo[de]isoquinolines possessing a free amino
 group
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D2CE00903J
_journal_year                    2022
_chemical_formula_sum            'C16 H17 N O7'
_chemical_formula_weight         335.30
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-06-28 deposited with the CCDC.	2022-07-29 downloaded from the CCDC.
;
_cell_angle_alpha                83.079(4)
_cell_angle_beta                 81.948(3)
_cell_angle_gamma                89.975(4)
_cell_formula_units_Z            4
_cell_length_a                   7.7282(7)
_cell_length_b                   9.9974(10)
_cell_length_c                   19.2246(17)
_cell_measurement_reflns_used    5609
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.03
_cell_measurement_theta_min      3.01
_cell_volume                     1459.8(2)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type
'Bruker KAPPA APEX II area-detector diffractometer'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0425
_diffrn_reflns_av_unetI/netI     0.0907
_diffrn_reflns_Laue_measured_fraction_full 0.993
_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       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            24899
_diffrn_reflns_point_group_measured_fraction_full 0.852
_diffrn_reflns_point_group_measured_fraction_max 0.823
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.999
_diffrn_reflns_theta_min         4.107
_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.879
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.526
_exptl_crystal_description       fragment
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.140
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details
;
 Flack x determined using 3103 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     877
_refine_ls_number_reflns         14009
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0861
_refine_ls_R_factor_gt           0.0573
_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^)+(0.0489P)^2^+0.3136P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1110
_refine_ls_wR_factor_ref         0.1242
_reflns_Friedel_coverage         0.654
_reflns_Friedel_fraction_full    0.711
_reflns_Friedel_fraction_max     0.651
_reflns_number_gt                10562
_reflns_number_total             14009
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ce00903j2.cif
_cod_data_source_block           Liza
_cod_database_code               7245296
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.953
_shelx_estimated_absorpt_t_max   0.983
_shelx_res_checksum              41999