#------------------------------------------------------------------------------
#$Date: 2020-06-06 04:11:42 +0300 (Sat, 06 Jun 2020) $
#$Revision: 252959 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/82/1558213.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_1558213
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         292.02
_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             2020-04-01T11:37:51-00:00
_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                92.7875(14)
_cell_angle_beta                 107.4969(10)
_cell_angle_gamma                114.3638(12)
_cell_formula_units_Z            2
_cell_length_a                   8.14797(10)
_cell_length_b                   9.89332(16)
_cell_length_c                   10.90921(11)
_cell_measurement_reflns_used    17759
_cell_measurement_temperature    250(2)
_cell_measurement_theta_max      76.888
_cell_measurement_theta_min      4.317
_cell_volume                     748.78(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      250(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 0.973
_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      -0.0955067
_diffrn_orient_matrix_UB_12      0.104859
_diffrn_orient_matrix_UB_13      -0.1137096
_diffrn_orient_matrix_UB_21      0.1431085
_diffrn_orient_matrix_UB_22      0.0783444
_diffrn_orient_matrix_UB_23      -0.0451432
_diffrn_orient_matrix_UB_31      0.1237935
_diffrn_orient_matrix_UB_32      -0.1152899
_diffrn_orient_matrix_UB_33      -0.0886507
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_unetI/netI     0.0408
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.973
_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            28413
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         77.205
_diffrn_reflns_theta_min         4.336
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.69
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.92433
_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    1.295
_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         0.156
_refine_diff_density_min         -0.137
_refine_diff_density_rms         0.03
_refine_ls_extinction_coef       0.0049(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   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         3097
_refine_ls_number_restraints     579
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0341
_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)+(0.0534P)²+0.0690P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0959
_refine_ls_wR_factor_ref         0.099
_reflns_Friedel_coverage         0
_reflns_number_gt                2797
_reflns_number_total             3097
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc02795b3.cif
_cod_data_source_block           BE75_BA25_250
_cod_original_cell_volume        748.778(19)
_cod_database_code               1558213
_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 0.16753(10) 0.15235(9) 0.30481(7) 0.0520(2) Uani 1 1 d . . . . .
H1 H 0.200052 0.17829 0.38528 0.078 Uiso 1 1 calc R U . . .
O2 O 0.82063(11) 0.22554(10) 0.43138(7) 0.0597(2) Uani 1 1 d . . . . .
H2A H 0.82493 0.26145 0.50329 0.09 Uiso 1 1 calc R U . . .
N1 N 0.26179(13) 0.24477(11) -0.43144(8) 0.0524(2) Uani 1 1 d . . . . .
C1 C 0.31771(14) 0.15045(10) 0.27619(9) 0.0422(2) Uani 1 1 d . . . . .
C2 C 0.49376(14) 0.18790(10) 0.37290(9) 0.0426(2) Uani 1 1 d . . . . .
H2 H 0.510764 0.214404 0.461327 0.051 Uiso 1 1 calc R U . . .
C3 C 0.64544(15) 0.18655(11) 0.34009(9) 0.0451(2) Uani 1 1 d . . . . .
C4 C 0.61948(17) 0.14469(12) 0.20904(10) 0.0522(3) Uani 1 1 d . . . . .
H4 H 0.720444 0.142106 0.185815 0.063 Uiso 1 1 calc R U . . .
C5 C 0.44316(18) 0.10720(12) 0.11429(10) 0.0546(3) Uani 1 1 d . . . . .
H5 H 0.425462 0.079524 0.025901 0.066 Uiso 1 1 calc R U . . .
C6 C 0.29144(16) 0.10909(11) 0.14542(10) 0.0501(3) Uani 1 1 d . . . . .
H6 H 0.172332 0.082801 0.079164 0.06 Uiso 1 1 calc R U . . .
C7 C 0.19672(16) 0.14748(13) -0.35739(10) 0.0522(3) Uani 1 1 d . . . . .
H7 H 0.155537 0.044152 -0.387516 0.063 Uiso 1 1 calc R U . . .
C8 C 0.18661(15) 0.19042(12) -0.23890(10) 0.0496(2) Uani 1 1 d . . . . .
H8 H 0.138653 0.117193 -0.190528 0.059 Uiso 1 1 calc R U . . .
C9 C 0.24743(14) 0.34202(12) -0.19126(9) 0.0443(2) Uani 1 1 d D U . . .
C10 C 0.32108(16) 0.44453(12) -0.26611(11) 0.0510(3) Uani 1 1 d . . . . .
H10 H 0.368438 0.548936 -0.236583 0.061 Uiso 1 1 calc R U . . .
C11 C 0.32386(16) 0.39140(13) -0.38399(11) 0.0539(3) Uani 1 1 d . . . . .
H11 H 0.372149 0.462159 -0.434134 0.065 Uiso 1 1 calc R U . . .
C12A C 0.2174(7) 0.3775(4) -0.0668(4) 0.0391(6) Uani 0.685(7) 1 d D U P A 1
H12A H 0.161752 0.297492 -0.026492 0.047 Uiso 0.685(7) 1 calc R U P A 1
C13A C 0.2667(4) 0.5189(3) -0.0110(2) 0.0376(5) Uani 0.685(7) 1 d D U P A 1
H13A H 0.325928 0.597684 -0.051295 0.045 Uiso 0.685(7) 1 calc R U P A 1
C12B C 0.271(5) 0.449(2) -0.084(2) 0.045(3) Uani 0.072(7) 1 d D U P A 2
H12B H 0.347862 0.550482 -0.082342 0.054 Uiso 0.072(7) 1 calc R U P A 2
C13B C 0.204(3) 0.428(2) 0.009(2) 0.047(3) Uani 0.072(7) 1 d D U P A 2
H13B H 0.132919 0.324617 0.007732 0.056 Uiso 0.072(7) 1 calc R U P A 2
C14A C 0.2349(8) 0.5612(4) 0.1106(4) 0.0372(8) Uani 0.685(7) 1 d DG U P A 1
C15A C 0.1495(8) 0.4535(3) 0.1780(4) 0.0421(8) Uani 0.685(7) 1 d G U P A 1
H15A H 0.112753 0.350838 0.148834 0.051 Uiso 0.685(7) 1 calc R U P A 1
C16A C 0.1185(8) 0.4977(4) 0.2885(4) 0.0427(8) Uani 0.685(7) 1 d G U P A 1
H16A H 0.060782 0.424899 0.334126 0.051 Uiso 0.685(7) 1 calc R U P A 1
N2A N 0.1729(8) 0.6496(4) 0.3317(4) 0.0446(10) Uani 0.685(7) 1 d G U P A 1
C17A C 0.2583(8) 0.7573(3) 0.2643(5) 0.0437(7) Uani 0.685(7) 1 d G U P A 1
H17A H 0.295017 0.860009 0.293442 0.052 Uiso 0.685(7) 1 calc R U P A 1
C18A C 0.2893(8) 0.7131(4) 0.1537(4) 0.0421(7) Uani 0.685(7) 1 d G U P A 1
H18A H 0.34699 0.785951 0.108149 0.051 Uiso 0.685(7) 1 calc R U P A 1
C14B C 0.213(2) 0.5262(13) 0.1158(10) 0.0491(19) Uani 0.315(7) 1 d D U P A 2
C15B C 0.133(2) 0.4482(9) 0.2028(12) 0.0514(18) Uani 0.315(7) 1 d . U P A 2
H15B H 0.084523 0.342402 0.191194 0.062 Uiso 0.315(7) 1 calc R U P A 2
C16B C 0.125(2) 0.5281(12) 0.3044(10) 0.0451(15) Uani 0.315(7) 1 d . U P A 2
H16B H 0.066701 0.467274 0.357164 0.054 Uiso 0.315(7) 1 calc R U P A 2
N2B N 0.179(2) 0.6611(11) 0.3402(11) 0.054(2) Uani 0.315(7) 1 d . U P A 2
C17B C 0.250(2) 0.7251(11) 0.2631(12) 0.0498(16) Uani 0.315(7) 1 d . U P A 2
H17B H 0.297516 0.830821 0.283201 0.06 Uiso 0.315(7) 1 calc R U P A 2
C18B C 0.2736(18) 0.6760(12) 0.1535(11) 0.0479(17) Uani 0.315(7) 1 d . U P A 2
H18B H 0.331021 0.745116 0.105171 0.058 Uiso 0.315(7) 1 calc R U P A 2
C19 C 0.246(3) 0.4054(18) -0.0767(15) 0.054(3) Uani 0.25 1 d D U P A 2
C20 C 0.2438(18) 0.474(2) 0.0117(10) 0.063(2) 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
1 -4 3 0.0598
-2 -6 -1 0.0374
0 3 6 0.0788
3 3 -4 0.0609
-5 0 0 0.0498
1 -4 -5 0.0636
-1 -2 -7 0.0688
-2 0 5 0.0662
-2 -5 2 0.0477
-5 -3 -4 0.0659
2 5 -2 0.0622
-2 -4 3 0.0581
-5 -4 -1 0.0318
5 4 1 0.0337
-1 4 4 0.0717
4 0 -2 0.0542
2 -4 0 0.0503
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 116.71(9) . . ?
O1 C1 C2 121.96(8) . . ?
O1 C1 C6 118.23(9) . . ?
C2 C1 C6 119.82(9) . . ?
C1 C2 C3 120.50(8) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
O2 C3 C2 122.25(8) . . ?
O2 C3 C4 117.91(9) . . ?
C2 C3 C4 119.84(10) . . ?
C5 C4 C3 118.82(10) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C4 C5 C6 121.95(9) . . ?
C4 C5 H5 119 . . ?
C6 C5 H5 119 . . ?
C5 C6 C1 119.05(10) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
N1 C7 C8 123.38(10) . . ?
N1 C7 H7 118.3 . . ?
C8 C7 H7 118.3 . . ?
C7 C8 C9 119.75(10) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C19 C9 C8 127.9(7) . . ?
C19 C9 C10 115.0(7) . . ?
C8 C9 C10 117.12(9) . . ?
C19 C9 C12B 16.5(4) . . ?
C8 C9 C12B 144.4(7) . . ?
C10 C9 C12B 98.5(7) . . ?
C8 C9 C12A 116.22(15) . . ?
C10 C9 C12A 126.59(16) . . ?
C11 C10 C9 119.18(10) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
N1 C11 C10 123.81(10) . . ?
N1 C11 H11 118.1 . . ?
C10 C11 H11 118.1 . . ?
C13A C12A C9 122.5(3) . . ?
C13A C12A H12A 118.7 . . ?
C9 C12A H12A 118.7 . . ?
C12A C13A C14A 125.1(3) . . ?
C12A C13A H13A 117.5 . . ?
C14A C13A H13A 117.5 . . ?
C13B C12B C9 131(2) . . ?
C13B C12B H12B 114.4 . . ?
C9 C12B H12B 114.4 . . ?
C12B C13B C14B 135(2) . . ?
C12B C13B H13B 112.7 . . ?
C14B C13B H13B 112.7 . . ?
C15A C14A C18A 120 . . ?
C15A C14A C13A 122.0(2) . . ?
C18A C14A C13A 118.0(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 . . ?
C16A N2A C17A 120 . . ?
C18A C17A N2A 120 . . ?
C18A C17A H17A 120 . . ?
N2A C17A H17A 120 . . ?
C17A C18A C14A 120 . . ?
C17A C18A H18A 120 . . ?
C14A C18A H18A 120 . . ?
C18B C14B C20 120.5(10) . . ?
C18B C14B C15B 109.5(5) . . ?
C20 C14B C15B 129.9(9) . . ?
C18B C14B C13B 137.1(10) . . ?
C20 C14B C13B 17.2(5) . . ?
C15B C14B C13B 113.4(9) . . ?
C16B C15B C14B 118.9(5) . . ?
C16B C15B H15B 120.6 . . ?
C14B C15B H15B 120.6 . . ?
N2B C16B C15B 132.7(6) . . ?
N2B C16B C17B 36.9(3) . . ?
C15B C16B C17B 95.8(4) . . ?
N2B C16B H16B 113.7 . . ?
C15B C16B H16B 113.7 . . ?
C17B C16B H16B 150.6 . . ?
C16B N2B C17B 106.6(6) . . ?
N2B C17B C18B 133.6(7) . . ?
N2B C17B C16B 36.5(4) . . ?
C18B C17B C16B 97.1(5) . . ?
N2B C17B H17B 113.2 . . ?
C18B C17B H17B 113.2 . . ?
C16B C17B H17B 149.7 . . ?
C14B C18B C17B 118.8(6) . . ?
C14B C18B H18B 120.6 . . ?
C17B C18B H18B 120.6 . . ?
C20 C19 C9 171(2) . . ?
C19 C20 C14B 168(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 1.3576(12) . ?
O1 H1 0.83 . ?
O2 C3 1.3535(13) . ?
O2 H2A 0.83 . ?
N1 C7 1.3313(15) . ?
N1 C11 1.3388(14) . ?
C1 C2 1.3862(14) . ?
C1 C6 1.3913(13) . ?
C2 C3 1.3910(14) . ?
C2 H2 0.94 . ?
C3 C4 1.3959(13) . ?
C4 C5 1.3784(16) . ?
C4 H4 0.94 . ?
C5 C6 1.3838(16) . ?
C5 H5 0.94 . ?
C6 H6 0.94 . ?
C7 C8 1.3776(14) . ?
C7 H7 0.94 . ?
C8 C9 1.3860(14) . ?
C8 H8 0.94 . ?
C9 C19 1.377(12) . ?
C9 C10 1.3887(16) . ?
C9 C12B 1.451(17) . ?
C9 C12A 1.500(4) . ?
C10 C11 1.3755(15) . ?
C10 H10 0.94 . ?
C11 H11 0.94 . ?
C12A C13A 1.340(4) . ?
C12A H12A 0.94 . ?
C13A C14A 1.499(3) . ?
C13A H13A 0.94 . ?
C12B C13B 1.268(18) . ?
C12B H12B 0.94 . ?
C13B C14B 1.447(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 1.351(8) . ?
C14B C20 1.356(12) . ?
C14B C15B 1.398(9) . ?
C15B C16B 1.361(8) . ?
C15B H15B 0.94 . ?
C16B N2B 1.203(9) . ?
C16B C17B 1.939(13) . ?
C16B H16B 0.94 . ?
N2B C17B 1.215(7) . ?
C17B C18B 1.367(7) . ?
C17B H17B 0.94 . ?
C18B H18B 0.94 . ?
C19 C20 1.159(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 2.7460(11) 175.7 1_556 yes
O2 H2A N2A^a 0.83 1.96 2.79(2) 177.2 2_666 yes
O2 H2A N2B^b 0.83 1.85 2.683(8) 176.9 2_666 yes
