#------------------------------------------------------------------------------
#$Date: 2019-11-17 14:03:33 +0200 (Sun, 17 Nov 2019) $
#$Revision: 230362 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/77/7057737.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_7057737
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             2018-05-21T16:00:19-00:00
_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                 111.539(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.3117(10)
_cell_length_b                   9.8022(5)
_cell_length_c                   14.2920(13)
_cell_measurement_reflns_used    1362
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      26.38
_cell_measurement_theta_min      2.84
_cell_volume                     1474.0(2)
_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      291(2)
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.995
_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  0.0506
_diffrn_reflns_av_unetI/netI     0.0901
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.995
_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            7800
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.556
_diffrn_reflns_theta_min         1.979
_exptl_absorpt_coefficient_mu    0.087
_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    1.317
_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         0.145
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.8
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3395
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.8
_refine_ls_R_factor_all          0.106
_refine_ls_R_factor_gt           0.0425
_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)+(0.0279P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0737
_refine_ls_wR_factor_ref         0.0877
_reflns_Friedel_coverage         0
_reflns_number_gt                1634
_reflns_number_total             3395
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8nj03815e2.cif
_cod_data_source_block           1_290K
_cod_depositor_comments
'Adding full bibliography for 7057732--7057737.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7057737
_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 0.09000(13) 0.14977(13) 0.47727(10) 0.0588(4) Uani 1 1 d . .
H1 H 0.025902 0.175206 0.486227 0.088 Uiso 1 1 calc R U
O2 O -0.05932(14) 0.46601(15) 0.20239(11) 0.0712(4) Uani 1 1 d . .
H2A H -0.116897 0.476103 0.2237 0.107 Uiso 1 1 calc R U
N1 N 0.11529(16) 0.77906(16) 0.47742(12) 0.0513(4) Uani 1 1 d . .
N2 N 0.73864(16) 0.52729(16) 0.26223(12) 0.0528(4) Uani 1 1 d . .
C1 C 0.09767(17) 0.21365(17) 0.39588(14) 0.0427(5) Uani 1 1 d . .
C2 C 0.00981(17) 0.30842(16) 0.34069(13) 0.0415(5) Uani 1 1 d . .
H2 H -0.05901 0.330441 0.358631 0.05 Uiso 1 1 calc R U
C3 C 0.02385(18) 0.37068(18) 0.25882(15) 0.0476(5) Uani 1 1 d . .
C4 C 0.12602(19) 0.33856(19) 0.23202(15) 0.0554(6) Uani 1 1 d . .
H4 H 0.135751 0.380511 0.176921 0.067 Uiso 1 1 calc R U
C5 C 0.21302(19) 0.2441(2) 0.28753(16) 0.0580(6) Uani 1 1 d . .
H5 H 0.281738 0.222226 0.269415 0.07 Uiso 1 1 calc R U
C6 C 0.20069(18) 0.18112(18) 0.36935(16) 0.0529(5) Uani 1 1 d . .
H6 H 0.260569 0.117535 0.406485 0.063 Uiso 1 1 calc R U
C7 C 0.2250(2) 0.84325(18) 0.52246(15) 0.0538(6) Uani 1 1 d . .
H7 H 0.223692 0.926337 0.55349 0.065 Uiso 1 1 calc R U
C8 C 0.34051(18) 0.79398(15) 0.52589(14) 0.0455(5) Uani 1 1 d . .
H8 H 0.414479 0.843197 0.55878 0.055 Uiso 1 1 calc R U
C9 C 0.34610(16) 0.67133(15) 0.48034(12) 0.0339(4) Uani 1 1 d . .
C10 C 0.23190(17) 0.60747(17) 0.43071(14) 0.0472(5) Uani 1 1 d . .
H10 H 0.229561 0.526363 0.396313 0.057 Uiso 1 1 calc R U
C11 C 0.12116(18) 0.66372(18) 0.43202(15) 0.0547(5) Uani 1 1 d . .
H11 H 0.04558 0.617383 0.398735 0.066 Uiso 1 1 calc R U
C12 C 0.47172(15) 0.60832(15) 0.49407(12) 0.0343(4) Uani 1 1 d . .
H12 H 0.535865 0.679308 0.502658 0.041 Uiso 1 1 calc R U
C13 C 0.47862(15) 0.50050(14) 0.41759(12) 0.0331(4) Uani 1 1 d . .
H13 H 0.392883 0.476416 0.371584 0.04 Uiso 1 1 calc R U
C14 C 0.56383(15) 0.52284(15) 0.36009(12) 0.0334(4) Uani 1 1 d . .
C15 C 0.54696(18) 0.44617(17) 0.27529(14) 0.0495(5) Uani 1 1 d . .
H15 H 0.475698 0.390716 0.248636 0.059 Uiso 1 1 calc R U
C16 C 0.6349(2) 0.45136(19) 0.23004(15) 0.0569(6) Uani 1 1 d . .
H16 H 0.620647 0.398035 0.173104 0.068 Uiso 1 1 calc R U
C17 C 0.75059(18) 0.60634(18) 0.34011(16) 0.0534(5) Uani 1 1 d . .
H17 H 0.820293 0.664553 0.362897 0.064 Uiso 1 1 calc R U
C18 C 0.66682(17) 0.60835(17) 0.38980(14) 0.0474(5) Uani 1 1 d . .
H18 H 0.680158 0.667706 0.443478 0.057 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 116.00(16) . .
C16 N2 C17 115.25(16) . .
O1 C1 C2 122.99(16) . .
O1 C1 C6 117.01(17) . .
C2 C1 C6 120.00(18) . .
C1 C2 C3 120.03(17) . .
C1 C2 H2 120 . .
C3 C2 H2 120 . .
O2 C3 C2 122.46(16) . .
O2 C3 C4 117.33(18) . .
C2 C3 C4 120.21(19) . .
C5 C4 C3 119.29(19) . .
C5 C4 H4 120.4 . .
C3 C4 H4 120.4 . .
C4 C5 C6 121.33(18) . .
C4 C5 H5 119.3 . .
C6 C5 H5 119.3 . .
C5 C6 C1 119.14(19) . .
C5 C6 H6 120.4 . .
C1 C6 H6 120.4 . .
N1 C7 C8 123.83(17) . .
N1 C7 H7 118.1 . .
C8 C7 H7 118.1 . .
C7 C8 C9 119.74(18) . .
C7 C8 H8 120.1 . .
C9 C8 H8 120.1 . .
C10 C9 C8 116.30(16) . .
C10 C9 C12 123.18(14) . .
C8 C9 C12 120.27(16) . .
C11 C10 C9 119.89(17) . .
C11 C10 H10 120.1 . .
C9 C10 H10 120.1 . .
N1 C11 C10 124.18(18) . .
N1 C11 H11 117.9 . .
C10 C11 H11 117.9 . .
C9 C12 C13 118.88(14) . .
C9 C12 C13 115.04(12) . 3_666
C13 C12 C13 90.46(11) . 3_666
C9 C12 H12 110.3 . .
C13 C12 H12 110.3 . .
C13 C12 H12 110.3 3_666 .
C14 C13 C12 119.98(13) . .
C14 C13 C12 115.07(13) . 3_666
C12 C13 C12 89.54(11) . 3_666
C14 C13 H13 110.2 . .
C12 C13 H13 110.2 . .
C12 C13 H13 110.2 3_666 .
C18 C14 C15 115.69(15) . .
C18 C14 C13 124.47(15) . .
C15 C14 C13 119.64(15) . .
C16 C15 C14 120.25(18) . .
C16 C15 H15 119.9 . .
C14 C15 H15 119.9 . .
N2 C16 C15 124.16(18) . .
N2 C16 H16 117.9 . .
C15 C16 H16 117.9 . .
N2 C17 C18 124.45(19) . .
N2 C17 H17 117.8 . .
C18 C17 H17 117.8 . .
C14 C18 C17 119.95(17) . .
C14 C18 H18 120 . .
C17 C18 H18 120 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.352(2) .
O1 H1 0.82 .
O2 C3 1.361(2) .
O2 H2A 0.82 .
N1 C11 1.317(2) .
N1 C7 1.328(2) .
N2 C16 1.321(2) .
N2 C17 1.322(2) .
C1 C2 1.377(2) .
C1 C6 1.388(2) .
C2 C3 1.380(2) .
C2 H2 0.93 .
C3 C4 1.381(2) .
C4 C5 1.372(3) .
C4 H4 0.93 .
C5 C6 1.374(3) .
C5 H5 0.93 .
C6 H6 0.93 .
C7 C8 1.377(2) .
C7 H7 0.93 .
C8 C9 1.380(2) .
C8 H8 0.93 .
C9 C10 1.375(2) .
C9 C12 1.495(2) .
C10 C11 1.375(2) .
C10 H10 0.93 .
C11 H11 0.93 .
C12 C13 1.543(2) .
C12 C13 1.590(2) 3_666
C12 H12 0.98 .
C13 C14 1.495(2) .
C13 H13 0.98 .
C14 C18 1.370(2) .
C14 C15 1.379(2) .
C15 C16 1.373(2) .
C15 H15 0.93 .
C16 H16 0.93 .
C17 C18 1.377(2) .
C17 H17 0.93 .
C18 H18 0.93 .
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 0.82 1.91 2.7207(18) 172.6 3_566
O2 H2A N2 0.82 1.97 2.7839(19) 170.9 1_455
