Covalent bond formation via a [2+2] cycloaddition reaction as a tool to alter thermal expansion parameters of organic co-crystals
Hutchins, Kristin M.; Unruh, Daniel K.; Groeneman, Ryan H.; New Journal of Chemistry 42 (2018) 16460–; doi:10.1039/C8NJ03815E

data_7057732
_publ_section_title
;
 Covalent bond formation via a [2+2] cycloaddition reaction as a tool to
 alter thermal expansion parameters of organic co-crystals
;
_journal_issue                   20
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              16460
_journal_paper_doi               10.1039/C8NJ03815E
_journal_volume                  42
_journal_year                    2018
_chemical_formula_sum            'C36 H32 N4 O4'
_chemical_formula_weight         584.65
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_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     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2018-05-21T15:57:10-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2018-07-30 deposited with the CCDC.
2018-09-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.822(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.3235(6)
_cell_length_b                   9.7491(3)
_cell_length_c                   14.2452(8)
_cell_measurement_reflns_used    1744
_cell_measurement_temperature    190(2)
_cell_measurement_theta_max      26.42
_cell_measurement_theta_min      2.85
_cell_volume                     1459.90(12)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      190(2)
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_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  0.0371
_diffrn_reflns_av_unetI/netI     0.0524
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7726
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.527
_diffrn_reflns_theta_min         1.977
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.8621
_exptl_absorpt_correction_T_min  0.7806
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.33
_exptl_crystal_description       rectangular
_exptl_crystal_F_000             616
_exptl_crystal_recrystallization_method Photoreaction
_exptl_crystal_size_max          0.355
_exptl_crystal_size_mid          0.264
_exptl_crystal_size_min          0.169
_refine_diff_density_max         0.2
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3356
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.078
_refine_ls_R_factor_gt           0.0463
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0460P)^2^+0.3269P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0992
_refine_ls_wR_factor_ref         0.115
_reflns_Friedel_coverage         0
_reflns_number_gt                2300
_reflns_number_total             3356
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8nj03815e2.cif
_cod_data_source_block           1_190K
_cod_depositor_comments
'Adding full bibliography for 7057732--7057737.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7057732
_shelx_estimated_absorpt_t_min   0.969
_shelx_estimated_absorpt_t_max   0.985
_shelx_res_checksum              95700
_shelx_hkl_checksum              67948