Novel pyrrolobenzodiazepine and pyrroloquinazoline scaffolds synthesized by a simple and highly selective Ugi/cyclization sequence
Garcia-Valverde, Maria; Pertejo, Pablo; Peña-Calleja, Pablo; Carreira-Barral, Israel; quesada, roberto; Cordero, Nicolás A.; Rodríguez, Francisco J.; Org. Biomol. Chem.  (2017) –; doi:10.1039/C7OB01807J

data_7155842
_publ_section_title
;
 Novel pyrrolobenzodiazepine and pyrroloquinazoline scaffolds synthesized
 by a simple and highly selective Ugi/cyclization sequence
;
_journal_name_full               'Org. Biomol. Chem.'
_journal_paper_doi               10.1039/C7OB01807J
_journal_year                    2017
_chemical_formula_moiety         'C23 H25 N3 O2'
_chemical_formula_sum            'C23 H25 N3 O2'
_chemical_formula_weight         375.46
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yc'
_space_group_name_H-M_alt        'P 1 c 1'
_symmetry_space_group_name_Hall  'P -2yc'
_symmetry_space_group_name_H-M   'P 1 c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2017-07-21 deposited with the CCDC.
2017-08-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.271(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.1046(8)
_cell_length_b                   15.0988(14)
_cell_length_c                   14.5408(15)
_cell_measurement_reflns_used    1874
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      21.06
_cell_measurement_theta_min      2.24
_cell_volume                     1995.6(3)
_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-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1179
_diffrn_reflns_av_unetI/netI     0.0788
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            63009
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.373
_diffrn_reflns_theta_min         1.946
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.9585
_exptl_absorpt_correction_T_min  0.6468
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2016/2'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.080
_exptl_transmission_factor_max   0.9585
_exptl_transmission_factor_min   0.6468
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.491
_refine_diff_density_rms         0.076
_refine_ls_abs_structure_details
;
 Flack x determined using 2523 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.4(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     505
_refine_ls_number_reflns         8051
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0880
_refine_ls_R_factor_gt           0.0618
_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^)+(0.0910P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1384
_refine_ls_wR_factor_ref         0.1561
_reflns_Friedel_coverage         0.978
_reflns_Friedel_fraction_full    0.988
_reflns_Friedel_fraction_max     0.981
_reflns_number_gt                6180
_reflns_number_total             8051
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob01807j2.cif
_cod_data_source_block           6c
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_database_code               7155842
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.975
_shelx_estimated_absorpt_t_max   0.994
_shelx_res_checksum              87205