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_1553246
_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_compound_source        synthetic
_chemical_formula_moiety         'C27 H36 N2 O3, 0.50 (H2 O)'
_chemical_formula_sum            'C27 H37 N2 O3.5'
_chemical_formula_weight         445.60
_chemical_melting_point          344.5(5)
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     other
_audit_creation_date             2017-10-31
_audit_creation_method           CRYSTALS_ver_14.61_build_6236
_cell_angle_alpha                90
_cell_angle_beta                 100.974(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   26.9572(8)
_cell_length_b                   9.9991(3)
_cell_length_c                   19.3387(5)
_cell_measurement_reflns_used    8202
_cell_measurement_temperature    150
_cell_measurement_theta_max      76
_cell_measurement_theta_min      5
_cell_volume                     5117.4(3)
_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    'Superflip (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.983
_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     1.54180
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_av_sigmaI/netI    0.0480
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_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            30975
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_diffrn_reflns_theta_max         76.787
_diffrn_reflns_theta_min         4.640
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_exptl_absorpt_correction_T_min  0.94
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, (Agilent, 2011)'
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_density_diffrn    1.157
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1928
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.88
_refine_diff_density_min         -0.62
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9954
_refine_ls_hydrogen_treatment    constr
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_refine_ls_number_reflns         10572
_refine_ls_number_restraints     1318
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_refine_ls_R_factor_gt           0.0692
_refine_ls_shift/su_max          0.0008193
_refine_ls_shift/su_mean         0.0000486
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.12P)^2^ + 3.27P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
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_refine_ls_wR_factor_gt          0.1871
_refine_ls_wR_factor_ref         0.2134
_reflns_limit_h_max              33
_reflns_limit_h_min              -33
_reflns_limit_k_max              12
_reflns_limit_k_min              0
_reflns_limit_l_max              24
_reflns_limit_l_min              0
_reflns_number_gt                8112
_reflns_number_total             10616
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   3.15
_oxford_diffrn_Wilson_scale      0.28
_oxford_refine_ls_r_factor_ref   0.0868
_oxford_refine_ls_scale          2.009(19)
_oxford_reflns_number_all        10579
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_oxford_structure_analysis_title 040eaa17
_cod_data_source_file            ed7b00982_si_003.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '344-345' was changed to
'344.5(5)' -- the average value was taken and precision was
estimated.

data item '_atom_sites_solution_primary' value 'Other' was changed to
'other' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

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_sg_symbol_H-M      'P 21/c'
_cod_original_formula_sum        'C27 H37 N2 O3.50'
_cod_database_code               1553246