#------------------------------------------------------------------------------
#$Date: 2019-11-17 14:03:33 +0200 (Sun, 17 Nov 2019) $
#$Revision: 230362 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/77/7057736.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7057736
loop_
_publ_author_name
'Hutchins, Kristin M.'
'Unruh, Daniel K.'
'Groeneman, Ryan H.'
_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             2018-05-21T15:59:34-00:00
_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                 111.658(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.3139(9)
_cell_length_b                   9.7762(5)
_cell_length_c                   14.2685(12)
_cell_measurement_reflns_used    1504
_cell_measurement_temperature    250(2)
_cell_measurement_theta_max      26.40
_cell_measurement_theta_min      2.84
_cell_volume                     1466.78(19)
_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      250(2)
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω 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  0.038
_diffrn_reflns_av_unetI/netI     0.0569
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.998
_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            7762
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.529
_diffrn_reflns_theta_min         1.978
_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    1.324
_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         0.163
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3383
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0933
_refine_ls_R_factor_gt           0.0486
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0494P)²+0.1072P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1021
_refine_ls_wR_factor_ref         0.1213
_reflns_Friedel_coverage         0
_reflns_number_gt                2088
_reflns_number_total             3383
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8nj03815e2.cif
_cod_data_source_block           1_250K
_cod_depositor_comments
'Adding full bibliography for 7057732--7057737.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7057736
_shelx_estimated_absorpt_t_min   0.97
_shelx_estimated_absorpt_t_max   0.985
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
O1 O 0.09025(14) 0.14989(14) 0.47747(11) 0.0500(4) Uani 1 1 d . .
H1 H 0.026722 0.177814 0.487611 0.075 Uiso 1 1 calc R U
O2 O -0.06063(15) 0.46609(16) 0.20117(12) 0.0603(4) Uani 1 1 d . .
H2A H -0.118343 0.477122 0.223242 0.09 Uiso 1 1 calc R U
N1 N 0.11477(16) 0.77880(16) 0.47729(12) 0.0444(4) Uani 1 1 d . .
N2 N 0.73796(17) 0.52794(16) 0.26177(13) 0.0450(4) Uani 1 1 d . .
C1 C 0.09786(17) 0.21357(18) 0.39594(14) 0.0370(4) Uani 1 1 d . .
C2 C 0.00921(17) 0.30879(17) 0.34025(14) 0.0355(4) Uani 1 1 d . .
H2 H -0.060325 0.331071 0.358389 0.043 Uiso 1 1 calc R U
C3 C 0.02299(18) 0.37096(19) 0.25809(15) 0.0408(5) Uani 1 1 d . .
C4 C 0.12525(19) 0.3385(2) 0.23089(16) 0.0464(5) Uani 1 1 d . .
H4 H 0.134664 0.380703 0.174841 0.056 Uiso 1 1 calc R U
C5 C 0.21255(19) 0.2442(2) 0.28678(16) 0.0483(5) Uani 1 1 d . .
H5 H 0.281797 0.221847 0.268289 0.058 Uiso 1 1 calc R U
C6 C 0.20106(18) 0.1816(2) 0.36902(16) 0.0453(5) Uani 1 1 d . .
H6 H 0.262223 0.117776 0.406846 0.054 Uiso 1 1 calc R U
C7 C 0.2246(2) 0.84381(19) 0.52234(15) 0.0452(5) Uani 1 1 d . .
H7 H 0.223327 0.92807 0.553681 0.054 Uiso 1 1 calc R U
C8 C 0.33971(19) 0.79458(17) 0.52555(15) 0.0397(5) Uani 1 1 d . .
H8 H 0.414451 0.844686 0.558724 0.048 Uiso 1 1 calc R U
C9 C 0.34568(16) 0.67149(16) 0.48007(13) 0.0293(4) Uani 1 1 d . .
C10 C 0.23150(17) 0.60624(19) 0.43088(15) 0.0408(5) Uani 1 1 d . .
H10 H 0.229476 0.523512 0.396749 0.049 Uiso 1 1 calc R U
C11 C 0.12074(19) 0.6623(2) 0.43184(16) 0.0476(5) Uani 1 1 d . .
H11 H 0.044378 0.615167 0.398139 0.057 Uiso 1 1 calc R U
C12 C 0.47171(16) 0.60882(16) 0.49412(13) 0.0293(4) Uani 1 1 d . .
H12 H 0.536389 0.680863 0.502778 0.035 Uiso 1 1 calc R U
C13 C 0.47830(16) 0.50058(16) 0.41747(13) 0.0285(4) Uani 1 1 d . .
H13 H 0.391556 0.47626 0.370882 0.034 Uiso 1 1 calc R U
C14 C 0.56369(15) 0.52309(16) 0.35951(12) 0.0292(4) Uani 1 1 d . .
C15 C 0.54648(19) 0.44611(19) 0.27463(14) 0.0421(5) Uani 1 1 d . .
H15 H 0.474479 0.389719 0.247938 0.051 Uiso 1 1 calc R U
C16 C 0.6337(2) 0.4512(2) 0.22880(15) 0.0492(5) Uani 1 1 d . .
H16 H 0.619 0.397505 0.170933 0.059 Uiso 1 1 calc R U
C17 C 0.75026(19) 0.6072(2) 0.33991(16) 0.0452(5) Uani 1 1 d . .
H17 H 0.820683 0.66637 0.362881 0.054 Uiso 1 1 calc R U
C18 C 0.66680(17) 0.60905(18) 0.38991(15) 0.0402(5) Uani 1 1 d . .
H18 H 0.680428 0.668816 0.44452 0.048 Uiso 1 1 calc R U
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C1 O1 H1 109.5 . .
C3 O2 H2A 109.5 . .
C11 N1 C7 116.09(16) . .
C17 N2 C16 115.66(15) . .
O1 C1 C2 122.81(16) . .
O1 C1 C6 117.43(18) . .
C2 C1 C6 119.76(18) . .
C3 C2 C1 119.93(16) . .
C3 C2 H2 120 . .
C1 C2 H2 120 . .
O2 C3 C2 122.44(16) . .
O2 C3 C4 117.22(17) . .
C2 C3 C4 120.34(19) . .
C5 C4 C3 119.16(19) . .
C5 C4 H4 120.4 . .
C3 C4 H4 120.4 . .
C6 C5 C4 121.48(18) . .
C6 C5 H5 119.3 . .
C4 C5 H5 119.3 . .
C5 C6 C1 119.3(2) . .
C5 C6 H6 120.3 . .
C1 C6 H6 120.3 . .
N1 C7 C8 123.62(18) . .
N1 C7 H7 118.2 . .
C8 C7 H7 118.2 . .
C7 C8 C9 120.01(19) . .
C7 C8 H8 120 . .
C9 C8 H8 120 . .
C10 C9 C8 116.33(16) . .
C10 C9 C12 123.14(15) . .
C8 C9 C12 120.23(16) . .
C11 C10 C9 119.85(17) . .
C11 C10 H10 120.1 . .
C9 C10 H10 120.1 . .
N1 C11 C10 124.06(19) . .
N1 C11 H11 118 . .
C10 C11 H11 118 . .
C9 C12 C13 118.61(14) . .
C9 C12 C13 115.09(13) . 3_666
C13 C12 C13 90.29(12) . 3_666
C9 C12 H12 110.5 . .
C13 C12 H12 110.5 . .
C13 C12 H12 110.5 3_666 .
C14 C13 C12 119.93(14) . .
C14 C13 C12 115.00(13) . 3_666
C12 C13 C12 89.71(12) . 3_666
C14 C13 H13 110.2 . .
C12 C13 H13 110.2 . .
C12 C13 H13 110.2 3_666 .
C18 C14 C15 116.14(16) . .
C18 C14 C13 124.09(15) . .
C15 C14 C13 119.55(16) . .
C16 C15 C14 120.42(19) . .
C16 C15 H15 119.8 . .
C14 C15 H15 119.8 . .
N2 C16 C15 123.55(18) . .
N2 C16 H16 118.2 . .
C15 C16 H16 118.2 . .
N2 C17 C18 124.41(19) . .
N2 C17 H17 117.8 . .
C18 C17 H17 117.8 . .
C14 C18 C17 119.59(18) . .
C14 C18 H18 120.2 . .
C17 C18 H18 120.2 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.350(2) .
O1 H1 0.83 .
O2 C3 1.361(2) .
O2 H2A 0.83 .
N1 C11 1.324(2) .
N1 C7 1.331(3) .
N2 C17 1.323(2) .
N2 C16 1.329(3) .
C1 C2 1.384(2) .
C1 C6 1.393(2) .
C2 C3 1.379(2) .
C2 H2 0.94 .
C3 C4 1.386(2) .
C4 C5 1.372(3) .
C4 H4 0.94 .
C5 C6 1.371(3) .
C5 H5 0.94 .
C6 H6 0.94 .
C7 C8 1.373(3) .
C7 H7 0.94 .
C8 C9 1.381(2) .
C8 H8 0.94 .
C9 C10 1.378(2) .
C9 C12 1.496(2) .
C10 C11 1.373(2) .
C10 H10 0.94 .
C11 H11 0.94 .
C12 C13 1.543(2) .
C12 C13 1.590(2) 3_666
C12 H12 0.99 .
C13 C14 1.502(2) .
C13 H13 0.99 .
C14 C18 1.372(2) .
C14 C15 1.377(2) .
C15 C16 1.372(3) .
C15 H15 0.94 .
C16 H16 0.94 .
C17 C18 1.378(2) .
C17 H17 0.94 .
C18 H18 0.94 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 N1 0.83 1.89 2.7182(19) 172.3 3_566
O2 H2A N2 0.83 1.96 2.786(2) 171.2 1_455
