#------------------------------------------------------------------------------
#$Date: 2019-11-17 14:03:33 +0200 (Sun, 17 Nov 2019) $
#$Revision: 230362 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/77/7057733.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_7057733
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             2018-05-21T15:57:38-00:00
_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                 111.746(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.3155(9)
_cell_length_b                   9.7527(5)
_cell_length_c                   14.2477(11)
_cell_measurement_reflns_used    1654
_cell_measurement_temperature    210(2)
_cell_measurement_theta_max      26.43
_cell_measurement_theta_min      2.85
_cell_volume                     1460.43(18)
_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      210(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  0.0384
_diffrn_reflns_av_unetI/netI     0.0559
_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            7750
_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         27.536
_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    1.33
_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         0.188
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3364
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0809
_refine_ls_R_factor_gt           0.0462
_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)+(0.0454P)²+0.1479P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0979
_refine_ls_wR_factor_ref         0.1136
_reflns_Friedel_coverage         0
_reflns_number_gt                2225
_reflns_number_total             3364
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8nj03815e2.cif
_cod_data_source_block           1_210K
_cod_depositor_comments
'Adding full bibliography for 7057732--7057737.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7057733
_shelx_estimated_absorpt_t_min   0.969
_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 0.09071(12) 0.15031(12) 0.47774(10) 0.0414(3) Uani 1 1 d . .
H1 H 0.025006 0.174893 0.485993 0.062 Uiso 1 1 calc R U
O2 O -0.06215(13) 0.46638(14) 0.19998(11) 0.0500(4) Uani 1 1 d . .
H2A H -0.120177 0.476881 0.221759 0.075 Uiso 1 1 calc R U
N1 N 0.11378(15) 0.77806(15) 0.47698(11) 0.0369(4) Uani 1 1 d . .
N2 N 0.73695(15) 0.52830(15) 0.26104(12) 0.0376(4) Uani 1 1 d . .
C1 C 0.09780(16) 0.21388(16) 0.39573(13) 0.0308(4) Uani 1 1 d . .
C2 C 0.00829(16) 0.30885(16) 0.33968(12) 0.0297(4) Uani 1 1 d . .
H2 H -0.061318 0.330667 0.357837 0.036 Uiso 1 1 calc R U
C3 C 0.02151(17) 0.37149(17) 0.25698(13) 0.0341(4) Uani 1 1 d . .
C4 C 0.12428(18) 0.33923(18) 0.22989(15) 0.0396(5) Uani 1 1 d . .
H4 H 0.133726 0.381849 0.173911 0.047 Uiso 1 1 calc R U
C5 C 0.21192(18) 0.24435(19) 0.28583(15) 0.0407(5) Uani 1 1 d . .
H5 H 0.280823 0.221731 0.266999 0.049 Uiso 1 1 calc R U
C6 C 0.20100(17) 0.18171(18) 0.36884(14) 0.0375(4) Uani 1 1 d . .
H6 H 0.262422 0.118026 0.4069 0.045 Uiso 1 1 calc R U
C7 C 0.22340(19) 0.84409(18) 0.52195(14) 0.0390(5) Uani 1 1 d . .
H7 H 0.221702 0.928671 0.553063 0.047 Uiso 1 1 calc R U
C8 C 0.33884(17) 0.79524(16) 0.52530(13) 0.0329(4) Uani 1 1 d . .
H8 H 0.413406 0.845934 0.558322 0.039 Uiso 1 1 calc R U
C9 C 0.34521(15) 0.67127(15) 0.47999(12) 0.0252(4) Uani 1 1 d . .
C10 C 0.23110(16) 0.60496(17) 0.43085(14) 0.0347(4) Uani 1 1 d . .
H10 H 0.229424 0.521863 0.396955 0.042 Uiso 1 1 calc R U
C11 C 0.11990(17) 0.66082(18) 0.43163(15) 0.0401(5) Uani 1 1 d . .
H11 H 0.043646 0.613153 0.398054 0.048 Uiso 1 1 calc R U
C12 C 0.47160(14) 0.60915(15) 0.49395(12) 0.0245(3) Uani 1 1 d . .
H12 H 0.536031 0.681597 0.502414 0.029 Uiso 1 1 calc R U
C13 C 0.47799(15) 0.50039(15) 0.41739(12) 0.0244(3) Uani 1 1 d . .
H13 H 0.391167 0.475895 0.370753 0.029 Uiso 1 1 calc R U
C14 C 0.56316(15) 0.52359(15) 0.35919(12) 0.0253(4) Uani 1 1 d . .
C15 C 0.54522(17) 0.44622(18) 0.27385(13) 0.0357(4) Uani 1 1 d . .
H15 H 0.472897 0.390124 0.246889 0.043 Uiso 1 1 calc R U
C16 C 0.63305(19) 0.45116(19) 0.22825(14) 0.0416(5) Uani 1 1 d . .
H16 H 0.618656 0.396798 0.170584 0.05 Uiso 1 1 calc R U
C17 C 0.75028(17) 0.60814(18) 0.33968(14) 0.0380(4) Uani 1 1 d . .
H17 H 0.82093 0.667152 0.362681 0.046 Uiso 1 1 calc R U
C18 C 0.66660(16) 0.60980(17) 0.38981(13) 0.0333(4) Uani 1 1 d . .
H18 H 0.680329 0.669602 0.444593 0.04 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 116.31(15) . .
C17 N2 C16 116.04(14) . .
O1 C1 C2 122.68(14) . .
O1 C1 C6 117.32(16) . .
C2 C1 C6 120.00(16) . .
C3 C2 C1 119.94(15) . .
C3 C2 H2 120 . .
C1 C2 H2 120 . .
O2 C3 C2 122.62(15) . .
O2 C3 C4 117.25(16) . .
C2 C3 C4 120.13(17) . .
C5 C4 C3 119.30(17) . .
C5 C4 H4 120.3 . .
C3 C4 H4 120.3 . .
C4 C5 C6 121.45(16) . .
C4 C5 H5 119.3 . .
C6 C5 H5 119.3 . .
C5 C6 C1 119.18(17) . .
C5 C6 H6 120.4 . .
C1 C6 H6 120.4 . .
N1 C7 C8 123.54(16) . .
N1 C7 H7 118.2 . .
C8 C7 H7 118.2 . .
C7 C8 C9 119.96(17) . .
C7 C8 H8 120 . .
C9 C8 H8 120 . .
C10 C9 C8 116.42(15) . .
C10 C9 C12 123.08(14) . .
C8 C9 C12 120.23(15) . .
C11 C10 C9 119.81(16) . .
C11 C10 H10 120.1 . .
C9 C10 H10 120.1 . .
N1 C11 C10 123.92(18) . .
N1 C11 H11 118 . .
C10 C11 H11 118 . .
C9 C12 C13 118.50(13) . .
C9 C12 C13 114.91(12) . 3_666
C13 C12 C13 90.16(11) . 3_666
C9 C12 H12 110.6 . .
C13 C12 H12 110.6 . .
C13 C12 H12 110.6 3_666 .
C14 C13 C12 119.62(13) . .
C14 C13 C12 115.14(12) . 3_666
C12 C13 C12 89.84(11) . 3_666
C14 C13 H13 110.2 . .
C12 C13 H13 110.2 . .
C12 C13 H13 110.2 3_666 .
C18 C14 C15 116.36(14) . .
C18 C14 C13 124.16(14) . .
C15 C14 C13 119.24(14) . .
C16 C15 C14 120.05(17) . .
C16 C15 H15 120 . .
C14 C15 H15 120 . .
N2 C16 C15 123.72(16) . .
N2 C16 H16 118.1 . .
C15 C16 H16 118.1 . .
N2 C17 C18 123.95(17) . .
N2 C17 H17 118 . .
C18 C17 H17 118 . .
C14 C18 C17 119.67(16) . .
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 1.351(2) .
O1 H1 0.83 .
O2 C3 1.357(2) .
O2 H2A 0.83 .
N1 C11 1.328(2) .
N1 C7 1.332(2) .
N2 C17 1.326(2) .
N2 C16 1.326(2) .
C1 C2 1.386(2) .
C1 C6 1.393(2) .
C2 C3 1.384(2) .
C2 H2 0.94 .
C3 C4 1.390(2) .
C4 C5 1.374(3) .
C4 H4 0.94 .
C5 C6 1.377(3) .
C5 H5 0.94 .
C6 H6 0.94 .
C7 C8 1.375(2) .
C7 H7 0.94 .
C8 C9 1.385(2) .
C8 H8 0.94 .
C9 C10 1.381(2) .
C9 C12 1.497(2) .
C10 C11 1.375(2) .
C10 H10 0.94 .
C11 H11 0.94 .
C12 C13 1.542(2) .
C12 C13 1.590(2) 3_666
C12 H12 0.99 .
C13 C14 1.503(2) .
C13 H13 0.99 .
C14 C18 1.374(2) .
C14 C15 1.381(2) .
C15 C16 1.375(2) .
C15 H15 0.94 .
C16 H16 0.94 .
C17 C18 1.381(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 2.7139(18) 172.2 3_566
O2 H2A N2 0.83 1.96 2.7847(18) 171.1 1_455
