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_1553247
_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         'C11 H12 Br1 N1 O2'
_chemical_formula_sum            'C11 H12 Br N O2'
_chemical_formula_weight         270.13
_chemical_melting_point          353
_space_group_IT_number           145
_space_group_name_Hall           'P 32'
_space_group_name_H-M_alt        'P 32'
_symmetry_cell_setting           trigonal
_symmetry_space_group_name_Hall  'P 32'
_symmetry_space_group_name_H-M   'P 32'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             2017-09-27
_audit_creation_method           CRYSTALS_ver_14.61_build_6236
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            3
_cell_length_a                   9.9756(3)
_cell_length_b                   9.9756(3)
_cell_length_c                   9.8502(3)
_cell_measurement_reflns_used    4387
_cell_measurement_temperature    150
_cell_measurement_theta_max      76
_cell_measurement_theta_min      5
_cell_volume                     848.89(4)
_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 0.998
_diffrn_measured_fraction_theta_max 0.994
_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  0.0190
_diffrn_reflns_av_sigmaI/netI    0.0249
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6737
_diffrn_reflns_theta_full        74.333
_diffrn_reflns_theta_max         75.850
_diffrn_reflns_theta_min         5.120
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.798
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_exptl_absorpt_correction_T_min  0.36
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, (Agilent, 2011)'
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_density_diffrn    1.585
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.37
_refine_diff_density_min         -0.28
_refine_ls_abs_structure_details 'Flack (1983), 1161 Friedel-pairs'
_refine_ls_abs_structure_Flack   -0.031(14)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         2334
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0189
_refine_ls_R_factor_gt           0.0188
_refine_ls_shift/su_max          0.0004205
_refine_ls_shift/su_mean         0.0000316
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.03P)^2^ + 0.26P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0493
_refine_ls_wR_factor_gt          0.0492
_refine_ls_wR_factor_ref         0.0493
_reflns_limit_h_max              6
_reflns_limit_h_min              -12
_reflns_limit_k_max              12
_reflns_limit_k_min              0
_reflns_limit_l_max              12
_reflns_limit_l_min              -12
_reflns_number_gt                2322
_reflns_number_total             2337
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.68
_oxford_diffrn_Wilson_scale      0.02
_oxford_refine_ls_r_factor_ref   0.0189
_oxford_refine_ls_scale          8.09(15)
_oxford_reflns_number_all        2334
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_oxford_structure_analysis_title 060eaa17
_cod_data_source_file            ed7b00982_si_003.cif
_cod_data_source_block           2
_cod_depositor_comments
;
The following automatic conversions were performed:

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_cell_volume        848.89(5)
_cod_original_formula_sum        'C11 H12 Br1 N1 O2'
_cod_database_code               1553247