Four Step Total Synthesis of an H3Receptor Antagonist Using Only Tools Found in a Typical Teaching Laboratory
Smith, Catherine J.; Mansfield, Steven J.; Anderson, Edward A.; Burton, Jonathan W.; Journal of Chemical Education 96 (2018) 137–; doi:10.1021/acs.jchemed.7b00982

data_1553248
_publ_section_title
;
 Four Step Total Synthesis of an H3Receptor Antagonist Using Only Tools
 Found in a Typical Teaching Laboratory
;
_journal_issue                   1
_journal_name_full               'Journal of Chemical Education'
_journal_page_first              137
_journal_paper_doi               10.1021/acs.jchemed.7b00982
_journal_volume                  96
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_compound_source        synthetic
_chemical_formula_moiety         'C17 H17 N1 O3'
_chemical_formula_sum            'C17 H17 N O3'
_chemical_formula_weight         283.33
_chemical_melting_point          503.5(5)
_space_group_IT_number           9
_space_group_name_Hall           'I -2ya'
_space_group_name_H-M_alt        'I 1 a 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'I -2ya'
_symmetry_space_group_name_H-M   'I 1 a 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             2017-08-23
_audit_creation_method           CRYSTALS_ver_14.61_build_6236
_cell_angle_alpha                90
_cell_angle_beta                 97.453(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.8846(4)
_cell_length_b                   9.7683(3)
_cell_length_c                   15.0513(6)
_cell_measurement_reflns_used    3900
_cell_measurement_temperature    150
_cell_measurement_theta_max      76
_cell_measurement_theta_min      5
_cell_volume                     1441.01(9)
_computing_cell_refinement       'CrysAlisPro, (Agilent, 2011)'
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_data_reduction        'CrysAlisPro, (Agilent, 2011)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0168
_diffrn_reflns_av_sigmaI/netI    0.0212
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5930
_diffrn_reflns_theta_full        73.701
_diffrn_reflns_theta_max         75.981
_diffrn_reflns_theta_min         5.412
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.728
_exptl_absorpt_correction_T_max  0.92
_exptl_absorpt_correction_T_min  0.75
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, (Agilent, 2011)'
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.14
_refine_diff_density_min         -0.15
_refine_ls_abs_structure_details 'Flack (1983), 805 Friedel-pairs'
_refine_ls_abs_structure_Flack   -0.17(16)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         2300
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0260
_refine_ls_R_factor_gt           0.0257
_refine_ls_shift/su_max          0.0002291
_refine_ls_shift/su_mean         0.0000406
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.04P)^2^ + 0.29P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0689
_refine_ls_wR_factor_gt          0.0684
_refine_ls_wR_factor_ref         0.0689
_reflns_limit_h_max              11
_reflns_limit_h_min              -12
_reflns_limit_k_max              12
_reflns_limit_k_min              0
_reflns_limit_l_max              17
_reflns_limit_l_min              -18
_reflns_number_gt                2272
_reflns_number_total             2306
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.82
_oxford_diffrn_Wilson_scale      0.02
_oxford_refine_ls_r_factor_ref   0.0260
_oxford_refine_ls_scale          7.7(2)
_oxford_reflns_number_all        2300
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_oxford_structure_analysis_title 030eaa17b
_cod_data_source_file            ed7b00982_si_003.cif
_cod_data_source_block           6
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '503-504' was changed to
'503.5(5)' -- the average value was taken and precision was
estimated.

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

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_formula_sum        'C17 H17 N1 O3'
_cod_database_code               1553248