Synthesis of N-substituted Pyrido[4,3-d]pyrimidines for the Large-Scale Production of Self-Assembled Rosettes and Nanotubes
Asuman Durmus; Gorkem Gunbas; Steven C. Farmer; Marilyn M. Olmstead; Mark Mascal; Belete Legese; Jae-Young Cho; Rachel L. Beingessner; Takeshi Yamazaki; Hicham Fenniri; Journal of Organic Chemistry 78 (2013) 11421–11426; doi:10.1021/jo4019792

data_4028760
_publ_section_title
;
 Synthesis of N-substituted Pyrido[4,3-d]pyrimidines for the Large-Scale
 Production of Self-Assembled Rosettes and Nanotubes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              11421
_journal_page_last               11426
_journal_paper_doi               10.1021/jo4019792
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C14 H21 N5 O2, C2 H6 O S'
_chemical_formula_sum            'C16 H27 N5 O3 S'
_chemical_formula_weight         369.48
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2012
_cell_angle_alpha                73.164(4)
_cell_angle_beta                 89.207(4)
_cell_angle_gamma                71.084(4)
_cell_formula_units_Z            6
_cell_length_a                   12.6924(8)
_cell_length_b                   14.0725(9)
_cell_length_c                   17.2084(11)
_cell_measurement_reflns_used    8087
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      70.02
_cell_measurement_theta_min      4.76
_cell_volume                     2772.1(3)
_computing_cell_refinement       'SAINT (Bruker, 2011)'
_computing_data_collection       'Apex 2 (Bruker, 2010)'
_computing_data_reduction        'SAINT (Bruker, 2011)'
_computing_publication_material  'SHELXL-2012 (Sheldrick, 2012)'
_computing_structure_refinement  'SHELXL-2012 (Sheldrick, 2012)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker ApexII'
_diffrn_measurement_method       \w
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.8856
_diffrn_reflns_av_R_equivalents  0.0479
_diffrn_reflns_av_unetI/netI     0.0887
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            20348
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        32.097
_diffrn_reflns_theta_max         32.250
_diffrn_reflns_theta_min         1.999
_diffrn_source                   'Beamline 11.3.1, ALS'
_exptl_absorpt_coefficient_mu    0.357
_exptl_absorpt_correction_T_max  0.747
_exptl_absorpt_correction_T_min  0.614
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_description       needle
_exptl_crystal_F_000             1188
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.010
_refine_diff_density_max         1.171
_refine_diff_density_min         -0.880
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     690
_refine_ls_number_reflns         9943
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.1021
_refine_ls_R_factor_gt           0.0748
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.1285P)^2^+0.5381P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2142
_refine_ls_wR_factor_ref         0.2313
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7038
_reflns_number_total             9943
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo4019792_si_002.cif
_cod_data_source_block           mn2130
_cod_database_code               4028760
_shelx_estimated_absorpt_t_min   0.925
_shelx_estimated_absorpt_t_max   0.996
_shelxl_version_number           2012-6
_shelx_res_checksum              18774