#------------------------------------------------------------------------------
#$Date: 2019-11-17 13:03:33 +0100 (dom 17 de nov de 2019) $
#$Revision: 230362 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/77/7057732.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_7057732
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             2018-05-21T15:57:10-00:00
_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       '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  0.0371
_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/[σ²(Fo²)+(0.0460P)²+0.3269P] where P=(Fo²+2Fc²)/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 > 2σ(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
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 0.09083(12) 0.15056(13) 0.47783(10) 0.0372(3) Uani 1 1 d . .
H1 H 0.023983 0.174804 0.485799 0.056 Uiso 1 1 calc R U
O2 O -0.06302(13) 0.46664(14) 0.19924(10) 0.0449(4) Uani 1 1 d . .
H2A H -0.120092 0.479389 0.222717 0.067 Uiso 1 1 calc R U
N1 N 0.11343(15) 0.77802(15) 0.47693(11) 0.0332(4) Uani 1 1 d . .
N2 N 0.73689(15) 0.52865(15) 0.26091(11) 0.0336(4) Uani 1 1 d . .
C1 C 0.09774(16) 0.21412(17) 0.39550(13) 0.0280(4) Uani 1 1 d . .
C2 C 0.00803(16) 0.30911(16) 0.33940(13) 0.0267(4) Uani 1 1 d . .
H2 H -0.062118 0.3313 0.357875 0.032 Uiso 1 1 calc R U
C3 C 0.02097(17) 0.37159(18) 0.25633(13) 0.0307(4) Uani 1 1 d . .
C4 C 0.12334(17) 0.33947(19) 0.22903(14) 0.0354(4) Uani 1 1 d . .
H4 H 0.132453 0.382379 0.172222 0.042 Uiso 1 1 calc R U
C5 C 0.21160(17) 0.24460(19) 0.28528(14) 0.0361(5) Uani 1 1 d . .
H5 H 0.281343 0.222039 0.266387 0.043 Uiso 1 1 calc R U
C6 C 0.20066(17) 0.18170(19) 0.36859(14) 0.0333(4) Uani 1 1 d . .
H6 H 0.262603 0.117126 0.407015 0.04 Uiso 1 1 calc R U
C7 C 0.22304(19) 0.84455(18) 0.52168(14) 0.0348(4) Uani 1 1 d . .
H7 H 0.221241 0.930244 0.552874 0.042 Uiso 1 1 calc R U
C8 C 0.33882(17) 0.79562(17) 0.52510(13) 0.0301(4) Uani 1 1 d . .
H8 H 0.414237 0.846861 0.55835 0.036 Uiso 1 1 calc R U
C9 C 0.34466(15) 0.67109(15) 0.47970(12) 0.0231(4) Uani 1 1 d . .
C10 C 0.23069(16) 0.60419(18) 0.43064(14) 0.0313(4) Uani 1 1 d . .
H10 H 0.229111 0.520145 0.396443 0.038 Uiso 1 1 calc R U
C11 C 0.11935(17) 0.65999(19) 0.43155(15) 0.0356(4) Uani 1 1 d . .
H11 H 0.042313 0.611576 0.397912 0.043 Uiso 1 1 calc R U
C12 C 0.47148(15) 0.60943(16) 0.49405(12) 0.0218(3) Uani 1 1 d . .
H12 H 0.536371 0.68283 0.50267 0.026 Uiso 1 1 calc R U
C13 C 0.47788(15) 0.50046(16) 0.41714(12) 0.0220(3) Uani 1 1 d . .
H13 H 0.390166 0.475671 0.369997 0.026 Uiso 1 1 calc R U
C14 C 0.56278(15) 0.52350(16) 0.35893(12) 0.0224(3) Uani 1 1 d . .
C15 C 0.54508(17) 0.44597(18) 0.27350(13) 0.0315(4) Uani 1 1 d . .
H15 H 0.472335 0.388737 0.246359 0.038 Uiso 1 1 calc R U
C16 C 0.63274(19) 0.45161(19) 0.22769(14) 0.0374(5) Uani 1 1 d . .
H16 H 0.617893 0.397327 0.169015 0.045 Uiso 1 1 calc R U
C17 C 0.75020(17) 0.60843(18) 0.33950(14) 0.0335(4) Uani 1 1 d . .
H17 H 0.821595 0.668086 0.362726 0.04 Uiso 1 1 calc R U
C18 C 0.66663(16) 0.61034(18) 0.38990(13) 0.0296(4) Uani 1 1 d . .
H18 H 0.680578 0.670822 0.44529 0.036 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 116.47(15) . .
C17 N2 C16 116.10(14) . .
O1 C1 C2 122.59(14) . .
O1 C1 C6 117.29(16) . .
C2 C1 C6 120.11(16) . .
C3 C2 C1 119.86(15) . .
C3 C2 H2 120.1 . .
C1 C2 H2 120.1 . .
O2 C3 C2 122.51(15) . .
O2 C3 C4 117.21(16) . .
C2 C3 C4 120.28(17) . .
C5 C4 C3 119.26(17) . .
C5 C4 H4 120.4 . .
C3 C4 H4 120.4 . .
C4 C5 C6 121.32(16) . .
C4 C5 H5 119.3 . .
C6 C5 H5 119.3 . .
C5 C6 C1 119.17(17) . .
C5 C6 H6 120.4 . .
C1 C6 H6 120.4 . .
N1 C7 C8 123.52(16) . .
N1 C7 H7 118.2 . .
C8 C7 H7 118.2 . .
C7 C8 C9 119.69(17) . .
C7 C8 H8 120.2 . .
C9 C8 H8 120.2 . .
C10 C9 C8 116.81(15) . .
C10 C9 C12 123.16(14) . .
C8 C9 C12 119.75(15) . .
C11 C10 C9 119.66(16) . .
C11 C10 H10 120.2 . .
C9 C10 H10 120.2 . .
N1 C11 C10 123.80(17) . .
N1 C11 H11 118.1 . .
C10 C11 H11 118.1 . .
C9 C12 C13 118.26(13) . .
C9 C12 C13 114.95(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 119.77(13) . .
C14 C13 C12 115.07(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 116.35(14) . .
C18 C14 C13 123.99(14) . .
C15 C14 C13 119.42(15) . .
C16 C15 C14 120.08(17) . .
C16 C15 H15 120 . .
C14 C15 H15 120 . .
N2 C16 C15 123.70(16) . .
N2 C16 H16 118.1 . .
C15 C16 H16 118.1 . .
N2 C17 C18 124.14(17) . .
N2 C17 H17 117.9 . .
C18 C17 H17 117.9 . .
C14 C18 C17 119.40(16) . .
C14 C18 H18 120.3 . .
C17 C18 H18 120.3 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.354(2) .
O1 H1 0.84 .
O2 C3 1.360(2) .
O2 H2A 0.84 .
N1 C11 1.334(2) .
N1 C7 1.334(2) .
N2 C17 1.325(2) .
N2 C16 1.328(2) .
C1 C2 1.387(2) .
C1 C6 1.392(2) .
C2 C3 1.386(2) .
C2 H2 0.95 .
C3 C4 1.389(2) .
C4 C5 1.379(3) .
C4 H4 0.95 .
C5 C6 1.382(3) .
C5 H5 0.95 .
C6 H6 0.95 .
C7 C8 1.379(2) .
C7 H7 0.95 .
C8 C9 1.389(2) .
C8 H8 0.95 .
C9 C10 1.382(2) .
C9 C12 1.499(2) .
C10 C11 1.378(2) .
C10 H10 0.95 .
C11 H11 0.95 .
C12 C13 1.547(2) .
C12 C13 1.593(2) 3_666
C12 H12 1 .
C13 C14 1.502(2) .
C13 H13 1 .
C14 C18 1.381(2) .
C14 C15 1.383(2) .
C15 C16 1.377(2) .
C15 H15 0.95 .
C16 H16 0.95 .
C17 C18 1.384(2) .
C17 H17 0.95 .
C18 H18 0.95 .
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 0.84 1.88 2.7125(18) 171.8 3_566
O2 H2A N2 0.84 1.95 2.7840(18) 171.5 1_455
