#------------------------------------------------------------------------------
#$Date: 2020-06-06 04:11:42 +0300 (Sat, 06 Jun 2020) $
#$Revision: 252959 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/82/1558214.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_1558214
loop_
_publ_author_name
'Ding, Xiaodan'
'Unruh, Daniel K.'
'Groeneman , Ryan'
'Hutchins, Kristin M.'
_publ_section_title
;
 Controlling thermal expansion within mixed cocrystals by tuning molecular
 motion capability
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D0SC02795B
_journal_year                    2020
_chemical_formula_sum            'C18.01 H15.51 N2 O2'
_chemical_formula_weight         291.96
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2020-04-01T11:37:03-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2020-04-08 deposited with the CCDC.	2020-06-05 downloaded from the CCDC.
;
_cell_angle_alpha                92.7008(14)
_cell_angle_beta                 107.5192(10)
_cell_angle_gamma                114.4022(12)
_cell_formula_units_Z            2
_cell_length_a                   8.13025(10)
_cell_length_b                   9.88487(15)
_cell_length_c                   10.90533(11)
_cell_measurement_reflns_used    18371
_cell_measurement_temperature    230(2)
_cell_measurement_theta_max      77.138
_cell_measurement_theta_min      4.324
_cell_volume                     746.12(2)
_computing_cell_refinement       'CrysAlisPro 1.171.40.65a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.65a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.65a (Rigaku OD, 2019)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      230(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.97
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0955542
_diffrn_orient_matrix_UB_12      0.1048056
_diffrn_orient_matrix_UB_13      -0.1136552
_diffrn_orient_matrix_UB_21      0.1433627
_diffrn_orient_matrix_UB_22      0.0786195
_diffrn_orient_matrix_UB_23      -0.0451013
_diffrn_orient_matrix_UB_31      0.1241247
_diffrn_orient_matrix_UB_32      -0.1153859
_diffrn_orient_matrix_UB_33      -0.0887973
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_av_unetI/netI     0.0391
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.97
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            28182
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.97
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         77.318
_diffrn_reflns_theta_min         4.337
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.692
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.92044
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        CrysAlisPro 1.171.40.65a (Rigaku Oxford Diffraction, 2019)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.3
_exptl_crystal_description       block
_exptl_crystal_F_000             307
_exptl_crystal_size_max          0.176
_exptl_crystal_size_mid          0.106
_exptl_crystal_size_min          0.066
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.152
_refine_diff_density_rms         0.031
_refine_ls_extinction_coef       0.0048(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         3084
_refine_ls_number_restraints     579
_refine_ls_restrained_S_all      0.991
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0335
_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)+(0.0527P)²+0.0785P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0937
_refine_ls_wR_factor_ref         0.0961
_reflns_Friedel_coverage         0
_reflns_number_gt                2814
_reflns_number_total             3084
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc02795b3.cif
_cod_data_source_block           BE75_BA25_230
_cod_original_cell_volume        746.122(18)
_cod_database_code               1558214
_shelx_estimated_absorpt_t_min   0.888
_shelx_estimated_absorpt_t_max   0.956
_shelx_shelxl_version_number     2018/3
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.16716(10) 0.15317(8) 0.30482(7) 0.0473(2) Uani 1 1 d . . . . .
H1 H 0.199514 0.178602 0.38534 0.071 Uiso 1 1 calc R U . . .
O2 O 0.82162(11) 0.22580(10) 0.43168(7) 0.0544(2) Uani 1 1 d . . . . .
H2A H 0.826075 0.262101 0.503483 0.082 Uiso 1 1 calc R U . . .
N1 N 0.26195(13) 0.24517(11) -0.43144(8) 0.0481(2) Uani 1 1 d . . . . .
C1 C 0.31754(14) 0.15100(10) 0.27631(9) 0.0385(2) Uani 1 1 d . . . . .
C2 C 0.49402(14) 0.18846(10) 0.37301(9) 0.0390(2) Uani 1 1 d . . . . .
H2 H 0.511157 0.215155 0.461433 0.047 Uiso 1 1 calc R U . . .
C3 C 0.64603(14) 0.18686(11) 0.34027(9) 0.0413(2) Uani 1 1 d . . . . .
C4 C 0.61988(16) 0.14484(12) 0.20907(10) 0.0476(3) Uani 1 1 d . . . . .
H4 H 0.721083 0.14229 0.185871 0.057 Uiso 1 1 calc R U . . .
C5 C 0.44316(17) 0.10721(12) 0.11428(10) 0.0500(3) Uani 1 1 d . . . . .
H5 H 0.425277 0.079146 0.025929 0.06 Uiso 1 1 calc R U . . .
C6 C 0.29102(16) 0.10952(11) 0.14539(9) 0.0458(2) Uani 1 1 d . . . . .
H6 H 0.171722 0.083488 0.07911 0.055 Uiso 1 1 calc R U . . .
C7 C 0.19667(15) 0.14710(12) -0.35744(10) 0.0475(2) Uani 1 1 d . . . . .
H7 H 0.155697 0.043776 -0.387637 0.057 Uiso 1 1 calc R U . . .
C8 C 0.18632(15) 0.18979(12) -0.23881(10) 0.0450(2) Uani 1 1 d . . . . .
H8 H 0.138156 0.116278 -0.190525 0.054 Uiso 1 1 calc R U . . .
C9 C 0.24718(13) 0.34149(11) -0.19096(9) 0.0402(2) Uani 1 1 d D U . . .
C10 C 0.32099(15) 0.44467(12) -0.26574(10) 0.0466(2) Uani 1 1 d . . . . .
H10 H 0.368222 0.549089 -0.236117 0.056 Uiso 1 1 calc R U . . .
C11 C 0.32399(15) 0.39184(13) -0.38389(10) 0.0490(3) Uani 1 1 d . . . . .
H11 H 0.372383 0.462874 -0.433986 0.059 Uiso 1 1 calc R U . . .
C12A C 0.2173(8) 0.3774(4) -0.0663(4) 0.0358(6) Uani 0.695(7) 1 d D U P A 1
H12A H 0.161871 0.297574 -0.025563 0.043 Uiso 0.695(7) 1 calc R U P A 1
C13A C 0.2668(4) 0.5193(3) -0.0112(2) 0.0338(5) Uani 0.695(7) 1 d D U P A 1
H13A H 0.326277 0.598002 -0.051617 0.041 Uiso 0.695(7) 1 calc R U P A 1
C12B C 0.268(5) 0.445(2) -0.084(2) 0.040(3) Uani 0.060(7) 1 d D U P A 2
H12B H 0.343501 0.54713 -0.085648 0.048 Uiso 0.060(7) 1 calc R U P A 2
C13B C 0.208(4) 0.431(2) 0.011(2) 0.040(3) Uani 0.060(7) 1 d D U P A 2
H13B H 0.13744 0.328371 0.011701 0.048 Uiso 0.060(7) 1 calc R U P A 2
C14A C 0.2343(8) 0.5617(4) 0.1102(4) 0.0329(7) Uani 0.695(7) 1 d DG U P A 1
C15A C 0.1492(8) 0.4538(3) 0.1779(4) 0.0384(8) Uani 0.695(7) 1 d G U P A 1
H15A H 0.112322 0.351053 0.148725 0.046 Uiso 0.695(7) 1 calc R U P A 1
C16A C 0.1188(8) 0.4979(4) 0.2887(4) 0.0388(8) Uani 0.695(7) 1 d G U P A 1
H16A H 0.06124 0.424994 0.334498 0.047 Uiso 0.695(7) 1 calc R U P A 1
N2A N 0.1733(8) 0.6499(4) 0.3319(4) 0.0408(10) Uani 0.695(7) 1 d G U P A 1
C17A C 0.2584(8) 0.7578(3) 0.2642(4) 0.0402(7) Uani 0.695(7) 1 d G U P A 1
H17A H 0.295278 0.860571 0.293363 0.048 Uiso 0.695(7) 1 calc R U P A 1
C18A C 0.2888(7) 0.7137(4) 0.1534(4) 0.0380(7) Uani 0.695(7) 1 d G U P A 1
H18A H 0.346362 0.786632 0.10759 0.046 Uiso 0.695(7) 1 calc R U P A 1
C14B C 0.216(2) 0.5269(13) 0.1170(10) 0.0447(19) Uani 0.305(7) 1 d D U P A 2
C15B C 0.133(2) 0.4483(9) 0.2027(11) 0.0464(17) Uani 0.305(7) 1 d . U P A 2
H15B H 0.084985 0.342424 0.191054 0.056 Uiso 0.305(7) 1 calc R U P A 2
C16B C 0.124(2) 0.5279(12) 0.3036(10) 0.0409(16) Uani 0.305(7) 1 d . U P A 2
H16B H 0.063991 0.466319 0.3555 0.049 Uiso 0.305(7) 1 calc R U P A 2
N2B N 0.177(2) 0.6607(11) 0.3402(10) 0.050(2) Uani 0.305(7) 1 d . U P A 2
C17B C 0.2491(19) 0.7260(12) 0.2637(12) 0.0443(16) Uani 0.305(7) 1 d . U P A 2
H17B H 0.296197 0.831646 0.283834 0.053 Uiso 0.305(7) 1 calc R U P A 2
C18B C 0.2760(18) 0.6777(12) 0.1546(11) 0.0432(17) Uani 0.305(7) 1 d . U P A 2
H18B H 0.334932 0.74727 0.106936 0.052 Uiso 0.305(7) 1 calc R U P A 2
C19 C 0.245(3) 0.4027(18) -0.0767(15) 0.048(3) Uani 0.25 1 d D U P A 2
C20 C 0.2463(17) 0.4760(19) 0.0118(10) 0.0560(19) Uani 0.25 1 d D U P A 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2 4 0 0.0556
-2 -6 -1 0.0374
0 3 6 0.0788
2 -4 0 0.0503
-5 0 0 0.0498
-1 -2 -7 0.0688
-5 -4 -1 0.0318
3 3 -4 0.0609
-2 -5 2 0.0477
1 -4 3 0.0598
2 5 -2 0.0622
-2 -4 3 0.0581
4 0 -2 0.0542
-2 0 5 0.0662
-1 4 4 0.0717
5 4 1 0.0337
-5 -3 -4 0.0659
1 -4 -5 0.0636
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
_geom_angle_publ_flag
C1 O1 H1 109.5 . . ?
C3 O2 H2A 109.5 . . ?
C7 N1 C11 116.83(9) . . ?
O1 C1 C2 122.00(8) . . ?
O1 C1 C6 118.17(9) . . ?
C2 C1 C6 119.84(9) . . ?
C1 C2 C3 120.54(8) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
O2 C3 C2 122.24(8) . . ?
O2 C3 C4 117.95(9) . . ?
C2 C3 C4 119.81(9) . . ?
C5 C4 C3 118.86(10) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C4 C5 C6 121.94(9) . . ?
C4 C5 H5 119 . . ?
C6 C5 H5 119 . . ?
C5 C6 C1 119.01(9) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
N1 C7 C8 123.25(10) . . ?
N1 C7 H7 118.4 . . ?
C8 C7 H7 118.4 . . ?
C7 C8 C9 119.80(10) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C19 C9 C8 127.3(7) . . ?
C19 C9 C10 115.5(7) . . ?
C8 C9 C10 117.17(9) . . ?
C19 C9 C12B 16.6(4) . . ?
C8 C9 C12B 143.9(7) . . ?
C10 C9 C12B 98.9(7) . . ?
C8 C9 C12A 116.52(17) . . ?
C10 C9 C12A 126.23(18) . . ?
C11 C10 C9 119.12(10) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
N1 C11 C10 123.78(10) . . ?
N1 C11 H11 118.1 . . ?
C10 C11 H11 118.1 . . ?
C13A C12A C9 122.4(3) . . ?
C13A C12A H12A 118.8 . . ?
C9 C12A H12A 118.8 . . ?
C12A C13A C14A 124.9(3) . . ?
C12A C13A H13A 117.6 . . ?
C14A C13A H13A 117.6 . . ?
C13B C12B C9 134(2) . . ?
C13B C12B H12B 112.8 . . ?
C9 C12B H12B 112.8 . . ?
C12B C13B C14B 138(2) . . ?
C12B C13B H13B 111 . . ?
C14B C13B H13B 111 . . ?
C15A C14A C18A 120 . . ?
C15A C14A C13A 121.9(2) . . ?
C18A C14A C13A 118.1(2) . . ?
C14A C15A C16A 120 . . ?
C14A C15A H15A 120 . . ?
C16A C15A H15A 120 . . ?
N2A C16A C15A 120 . . ?
N2A C16A H16A 120 . . ?
C15A C16A H16A 120 . . ?
C17A N2A C16A 120 . . ?
N2A C17A C18A 120 . . ?
N2A C17A H17A 120 . . ?
C18A C17A H17A 120 . . ?
C17A C18A C14A 120 . . ?
C17A C18A H18A 120 . . ?
C14A C18A H18A 120 . . ?
C18B C14B C20 119.8(10) . . ?
C18B C14B C15B 109.8(5) . . ?
C20 C14B C15B 130.4(9) . . ?
C18B C14B C13B 136.3(10) . . ?
C20 C14B C13B 17.2(4) . . ?
C15B C14B C13B 113.8(9) . . ?
C16B C15B C14B 118.6(5) . . ?
C16B C15B H15B 120.7 . . ?
C14B C15B H15B 120.7 . . ?
N2B C16B C15B 133.4(6) . . ?
N2B C16B C17B 37.2(4) . . ?
C15B C16B C17B 96.2(4) . . ?
N2B C16B H16B 113.3 . . ?
C15B C16B H16B 113.3 . . ?
C17B C16B H16B 150.5 . . ?
C16B N2B C17B 106.2(7) . . ?
N2B C17B C18B 133.5(7) . . ?
N2B C17B C16B 36.6(4) . . ?
C18B C17B C16B 97.0(5) . . ?
N2B C17B H17B 113.2 . . ?
C18B C17B H17B 113.2 . . ?
C16B C17B H17B 149.8 . . ?
C14B C18B C17B 118.4(6) . . ?
C14B C18B H18B 120.8 . . ?
C17B C18B H18B 120.8 . . ?
C20 C19 C9 169(2) . . ?
C19 C20 C14B 166(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.3571(12) . ?
O1 H1 0.83 . ?
O2 C3 1.3538(12) . ?
O2 H2A 0.83 . ?
N1 C7 1.3338(14) . ?
N1 C11 1.3389(14) . ?
C1 C2 1.3861(13) . ?
C1 C6 1.3927(13) . ?
C2 C3 1.3915(13) . ?
C2 H2 0.94 . ?
C3 C4 1.3974(13) . ?
C4 C5 1.3781(16) . ?
C4 H4 0.94 . ?
C5 C6 1.3859(16) . ?
C5 H5 0.94 . ?
C6 H6 0.94 . ?
C7 C8 1.3793(14) . ?
C7 H7 0.94 . ?
C8 C9 1.3869(14) . ?
C8 H8 0.94 . ?
C9 C19 1.368(13) . ?
C9 C10 1.3902(15) . ?
C9 C12B 1.435(18) . ?
C9 C12A 1.502(4) . ?
C10 C11 1.3782(15) . ?
C10 H10 0.94 . ?
C11 H11 0.94 . ?
C12A C13A 1.341(5) . ?
C12A H12A 0.94 . ?
C13A C14A 1.499(3) . ?
C13A H13A 0.94 . ?
C12B C13B 1.265(18) . ?
C12B H12B 0.94 . ?
C13B C14B 1.430(17) . ?
C13B H13B 0.94 . ?
C14A C15A 1.39 . ?
C14A C18A 1.39 . ?
C15A C16A 1.39 . ?
C15A H15A 0.94 . ?
C16A N2A 1.39 . ?
C16A H16A 0.94 . ?
N2A C17A 1.39 . ?
C17A C18A 1.39 . ?
C17A H17A 0.94 . ?
C18A H18A 0.94 . ?
C14B C18B 1.359(8) . ?
C14B C20 1.362(12) . ?
C14B C15B 1.393(9) . ?
C15B C16B 1.360(8) . ?
C15B H15B 0.94 . ?
C16B N2B 1.203(9) . ?
C16B C17B 1.938(14) . ?
C16B H16B 0.94 . ?
N2B C17B 1.220(8) . ?
C17B C18B 1.372(7) . ?
C17B H17B 0.94 . ?
C18B H18B 0.94 . ?
C19 C20 1.174(14) . ?
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
_geom_hbond_publ_flag
O1 H1 N1 0.83 1.92 2.7447(11) 175.6 1_556 yes
O2 H2A N2A^a 0.83 1.96 2.78(2) 177.2 2_666 yes
O2 H2A N2B^b 0.83 1.85 2.675(8) 177.2 2_666 yes
