Crystal Structure Prediction of Aminols: Advantages of a Supramolecular Synthon Approach with Experimental Structures
Archan Dey; Michael T. Kirchner; Venu R. Vangala; Gautam R. Desiraju; Raju Mondal; Judith A. K. Howard; Journal of the American Chemical Society 127 (2005) 10545–10559; doi:10.1021/ja042738c

data_4111842
_publ_contact_author_address
;
School of Chemistry
University of Hyderabad
Hyderabad 500 046
India
;
_publ_contact_author_email       desiraju@uohyd.ernet.in
_publ_contact_author_fax         '91 40 23010567'
_publ_contact_author_name        'Professor Gautam R. Desiraju'
_publ_contact_author_phone       '91 40 23134828'
_publ_section_title
;
 Crystal Structure Prediction of Aminols: Advantages of a Supramolecular
 Synthon Approach with Experimental Structures
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              10545
_journal_page_last               10559
_journal_paper_doi               10.1021/ja042738c
_journal_volume                  127
_journal_year                    2005
_chemical_formula_moiety         'C10 H9 N O'
_chemical_formula_sum            'C10 H9 N O'
_chemical_formula_weight         159.18
_chemical_melting_point          477
_chemical_name_common            8A2HNAP
_chemical_name_systematic
; 
 8-Amino-2-naphthol
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 108.804(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.415(2)
_cell_length_b                   4.1719(7)
_cell_length_c                   15.511(3)
_cell_measurement_reflns_used    1839
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.04
_cell_measurement_theta_min      2.55
_cell_volume                     760.5(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Nonius SMART APEX CCD area detector'
_diffrn_measurement_method
; 
Five runs in omega with phi= 0, 240, 120, 180 and 90 deg
and 611, 613, 362, 224 and 114 frames of 0.3 deg width and 5 sec duration, 
respectively.
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0452
_diffrn_reflns_av_sigmaI/netI    0.0395
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            5450
_diffrn_reflns_theta_full        26.05
_diffrn_reflns_theta_max         26.05
_diffrn_reflns_theta_min         1.84
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.9910
_exptl_absorpt_correction_T_min  0.6653
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
; 
empirical absobtion correction by SADABS 2.1. 
SADABS is run with 0.002 as restraint to the scale factor esd and 
1/4 as orders of spherical harmonics. R(int) drops from 7.23% to 3.98%. The 
scale factor is between 1.15 and 0.85. In the best error model factor g was 
0.0488 and was once refinded manually. All five runs are 
similar in R(int) and k 
factor. The transmission ratio is 0.671276  and a spherical 
absorbtion correctio 
is not applied.  Theoretical values for minimum and maximum transmission based 
on the size of the crystal are 0.9724 and 0.9910. 
;
_exptl_crystal_colour            Pink
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_description       Block
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     121
_refine_ls_number_reflns         1497
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0691
_refine_ls_R_factor_gt           0.0564
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0882P)^2^+0.2086P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1442
_refine_ls_wR_factor_ref         0.1533
_reflns_number_gt                1214
_reflns_number_total             1497
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja042738csi20050407_114233_12.cif
_cod_data_source_block           12
_cod_database_code               4111842