#------------------------------------------------------------------------------
#$Date: 2020-06-06 04:11:42 +0300 (Sat, 06 Jun 2020) $
#$Revision: 252959 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/82/1558211.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_1558211
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         291.92
_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             2020-04-01T11:35:11-00:00
_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                92.5280(17)
_cell_angle_beta                 107.5880(12)
_cell_angle_gamma                114.4693(14)
_cell_formula_units_Z            2
_cell_length_a                   8.09764(12)
_cell_length_b                   9.86690(19)
_cell_length_c                   10.89543(13)
_cell_measurement_reflns_used    19321
_cell_measurement_temperature    190(2)
_cell_measurement_theta_max      77.102
_cell_measurement_theta_min      4.326
_cell_volume                     740.79(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      190(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.971
_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      -0.0955558
_diffrn_orient_matrix_UB_12      0.1047296
_diffrn_orient_matrix_UB_13      -0.1136007
_diffrn_orient_matrix_UB_21      0.144325
_diffrn_orient_matrix_UB_22      0.0786799
_diffrn_orient_matrix_UB_23      -0.0453694
_diffrn_orient_matrix_UB_31      0.1242606
_diffrn_orient_matrix_UB_32      -0.1158965
_diffrn_orient_matrix_UB_33      -0.0889297
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.028
_diffrn_reflns_av_unetI/netI     0.0388
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.971
_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            27916
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         77.292
_diffrn_reflns_theta_min         4.34
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.697
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.90939
_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    1.308
_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         0.175
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.031
_refine_ls_extinction_coef       0.0043(7)
_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   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         3058
_refine_ls_number_restraints     579
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.0339
_refine_ls_R_factor_gt           0.0321
_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)+(0.0500P)²+0.0960P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0903
_refine_ls_wR_factor_ref         0.0919
_reflns_Friedel_coverage         0
_reflns_number_gt                2829
_reflns_number_total             3058
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc02795b3.cif
_cod_data_source_block           BE75_BA25_190
_cod_database_code               1558211
_shelx_estimated_absorpt_t_min   0.887
_shelx_estimated_absorpt_t_max   0.955
_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 0.16626(10) 0.15442(8) 0.30497(6) 0.03834(18) Uani 1 1 d . . . . .
H1 H 0.19917 0.179755 0.38655 0.058 Uiso 1 1 calc R U . . .
O2 O 0.82352(10) 0.22603(9) 0.43239(7) 0.0440(2) Uani 1 1 d . . . . .
H2A H 0.828209 0.26322 0.504933 0.066 Uiso 1 1 calc R U . . .
N1 N 0.26228(12) 0.24569(10) -0.43144(8) 0.0393(2) Uani 1 1 d . . . . .
C1 C 0.31706(13) 0.15188(9) 0.27634(9) 0.0316(2) Uani 1 1 d . . . . .
C2 C 0.49449(13) 0.18925(10) 0.37346(8) 0.0320(2) Uani 1 1 d . . . . .
H2 H 0.511942 0.216349 0.462846 0.038 Uiso 1 1 calc R U . . .
C3 C 0.64717(14) 0.18726(10) 0.34067(9) 0.0339(2) Uani 1 1 d . . . . .
C4 C 0.62070(15) 0.14481(11) 0.20941(9) 0.0391(2) Uani 1 1 d . . . . .
H4 H 0.723257 0.141848 0.186047 0.047 Uiso 1 1 calc R U . . .
C5 C 0.44273(16) 0.10723(11) 0.11421(9) 0.0409(2) Uani 1 1 d . . . . .
H5 H 0.424408 0.078682 0.024887 0.049 Uiso 1 1 calc R U . . .
C6 C 0.29013(15) 0.10999(11) 0.14536(9) 0.0376(2) Uani 1 1 d . . . . .
H6 H 0.168981 0.083704 0.07833 0.045 Uiso 1 1 calc R U . . .
C7 C 0.19672(14) 0.14664(12) -0.35767(10) 0.0390(2) Uani 1 1 d . . . . .
H7 H 0.155513 0.042211 -0.388423 0.047 Uiso 1 1 calc R U . . .
C8 C 0.18578(14) 0.18851(11) -0.23861(9) 0.0365(2) Uani 1 1 d . . . . .
H8 H 0.136779 0.113648 -0.189985 0.044 Uiso 1 1 calc R U . . .
C9 C 0.24692(13) 0.34081(11) -0.19044(9) 0.0328(2) Uani 1 1 d D U . . .
C10 C 0.32135(14) 0.44492(11) -0.26515(10) 0.0380(2) Uani 1 1 d . . . . .
H10 H 0.369369 0.550564 -0.234989 0.046 Uiso 1 1 calc R U . . .
C11 C 0.32443(14) 0.39259(12) -0.38358(10) 0.0401(2) Uani 1 1 d . . . . .
H11 H 0.373446 0.4649 -0.43416 0.048 Uiso 1 1 calc R U . . .
C12A C 0.2178(8) 0.3774(4) -0.0656(4) 0.0290(6) Uani 0.715(7) 1 d D U P A 1
H12A H 0.162136 0.296767 -0.02373 0.035 Uiso 0.715(7) 1 calc R U P A 1
C13A C 0.2676(4) 0.5199(3) -0.0109(2) 0.0274(5) Uani 0.715(7) 1 d D U P A 1
H13A H 0.32798 0.599711 -0.051943 0.033 Uiso 0.715(7) 1 calc R U P A 1
C12B C 0.272(7) 0.437(3) -0.081(4) 0.031(4) Uani 0.039(7) 1 d D U P A 2
H12B H 0.369723 0.535076 -0.074815 0.037 Uiso 0.039(7) 1 calc R U P A 2
C13B C 0.212(7) 0.440(3) 0.012(4) 0.035(4) Uani 0.039(7) 1 d D U P A 2
H13B H 0.127678 0.337784 0.011615 0.042 Uiso 0.039(7) 1 calc R U P A 2
C14A C 0.2343(8) 0.5616(4) 0.1105(4) 0.0278(7) Uani 0.715(7) 1 d DG U P A 1
C15A C 0.1487(8) 0.4535(3) 0.1784(4) 0.0316(7) Uani 0.715(7) 1 d G U P A 1
H15A H 0.11131 0.349484 0.149202 0.038 Uiso 0.715(7) 1 calc R U P A 1
C16A C 0.1177(8) 0.4977(3) 0.2890(4) 0.0319(8) Uani 0.715(7) 1 d G U P A 1
H16A H 0.059204 0.423905 0.335403 0.038 Uiso 0.715(7) 1 calc R U P A 1
N2A N 0.1724(9) 0.6500(4) 0.3317(4) 0.0338(9) Uani 0.715(7) 1 d G U P A 1
C17A C 0.2580(8) 0.7580(3) 0.2638(5) 0.0317(7) Uani 0.715(7) 1 d G U P A 1
H17A H 0.295417 0.862107 0.292958 0.038 Uiso 0.715(7) 1 calc R U P A 1
C18A C 0.2890(8) 0.7138(4) 0.1532(4) 0.0311(7) Uani 0.715(7) 1 d G U P A 1
H18A H 0.347524 0.787689 0.106757 0.037 Uiso 0.715(7) 1 calc R U P A 1
C14B C 0.218(2) 0.5318(14) 0.1158(12) 0.039(2) Uani 0.285(7) 1 d D U P A 2
C15B C 0.134(2) 0.4505(10) 0.2015(12) 0.0396(19) Uani 0.285(7) 1 d . U P A 2
H15B H 0.084556 0.343209 0.188761 0.047 Uiso 0.285(7) 1 calc R U P A 2
C16B C 0.124(2) 0.5282(12) 0.3026(11) 0.0320(16) Uani 0.285(7) 1 d . U P A 2
H16B H 0.063347 0.464635 0.354764 0.038 Uiso 0.285(7) 1 calc R U P A 2
N2B N 0.176(2) 0.6610(11) 0.3404(12) 0.040(2) Uani 0.285(7) 1 d . U P A 2
C17B C 0.249(2) 0.7275(13) 0.2655(14) 0.0362(16) Uani 0.285(7) 1 d . U P A 2
H17B H 0.296831 0.834382 0.287455 0.043 Uiso 0.285(7) 1 calc R U P A 2
C18B C 0.277(2) 0.6824(13) 0.1557(12) 0.0352(17) Uani 0.285(7) 1 d . U P A 2
H18B H 0.336166 0.754681 0.108419 0.042 Uiso 0.285(7) 1 calc R U P A 2
C19 C 0.242(3) 0.4017(18) -0.0786(15) 0.040(2) Uani 0.25 1 d D U P A 2
C20 C 0.2446(17) 0.4764(18) 0.0109(10) 0.0473(18) 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 4 0.0717
5 4 1 0.0337
-2 -4 3 0.0581
2 5 -2 0.0622
-5 -3 -4 0.0659
-2 -5 2 0.0477
-2 0 5 0.0662
-5 -4 -1 0.0318
-1 -2 -7 0.0688
1 -4 -5 0.0636
-5 0 0 0.0498
2 -4 0 0.0503
3 3 -4 0.0609
0 3 6 0.0788
-2 -6 -1 0.0374
4 0 -2 0.0542
1 -4 3 0.0598
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 116.92(8) . . ?
O1 C1 C2 121.84(8) . . ?
O1 C1 C6 118.23(8) . . ?
C2 C1 C6 119.92(9) . . ?
C1 C2 C3 120.44(8) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
O2 C3 C2 122.14(8) . . ?
O2 C3 C4 118.01(9) . . ?
C2 C3 C4 119.86(9) . . ?
C5 C4 C3 118.84(9) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C4 C5 C6 121.89(8) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C5 C6 C1 119.04(9) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
N1 C7 C8 123.24(9) . . ?
N1 C7 H7 118.4 . . ?
C8 C7 H7 118.4 . . ?
C7 C8 C9 119.66(9) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 H8 120.2 . . ?
C19 C9 C8 127.8(7) . . ?
C19 C9 C10 115.0(7) . . ?
C8 C9 C10 117.20(9) . . ?
C19 C9 C12B 13.9(8) . . ?
C8 C9 C12B 141.2(12) . . ?
C10 C9 C12B 101.5(11) . . ?
C8 C9 C12A 116.94(17) . . ?
C10 C9 C12A 125.79(17) . . ?
C11 C10 C9 119.11(9) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
N1 C11 C10 123.82(9) . . ?
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 124.4(3) . . ?
C12A C13A H13A 117.8 . . ?
C14A C13A H13A 117.8 . . ?
C13B C12B C9 143(3) . . ?
C13B C12B H12B 108.6 . . ?
C9 C12B H12B 108.6 . . ?
C12B C13B C14B 145(3) . . ?
C12B C13B H13B 107.3 . . ?
C14B C13B H13B 107.3 . . ?
C15A C14A C18A 120 . . ?
C15A C14A C13A 122.3(2) . . ?
C18A C14A C13A 117.7(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 . . ?
C20 C14B C18B 123.1(11) . . ?
C20 C14B C13B 14.7(8) . . ?
C18B C14B C13B 137.3(14) . . ?
C20 C14B C15B 127.9(10) . . ?
C18B C14B C15B 109.0(5) . . ?
C13B C14B C15B 113.6(12) . . ?
C16B C15B C14B 118.7(5) . . ?
C16B C15B H15B 120.7 . . ?
C14B C15B H15B 120.7 . . ?
N2B C16B C15B 133.6(6) . . ?
N2B C16B C17B 37.0(4) . . ?
C15B C16B C17B 96.6(4) . . ?
N2B C16B H16B 113.2 . . ?
C15B C16B H16B 113.2 . . ?
C17B C16B H16B 150.2 . . ?
C16B N2B C17B 106.0(7) . . ?
N2B C17B C18B 134.0(8) . . ?
N2B C17B C16B 36.9(4) . . ?
C18B C17B C16B 97.1(5) . . ?
N2B C17B H17B 113 . . ?
C18B C17B H17B 113 . . ?
C16B C17B H17B 149.9 . . ?
C14B C18B C17B 118.6(6) . . ?
C14B C18B H18B 120.7 . . ?
C17B C18B H18B 120.7 . . ?
C20 C19 C9 169(2) . . ?
C19 C20 C14B 167(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 1.3579(11) . ?
O1 H1 0.84 . ?
O2 C3 1.3548(12) . ?
O2 H2A 0.84 . ?
N1 C7 1.3343(14) . ?
N1 C11 1.3404(13) . ?
C1 C2 1.3885(13) . ?
C1 C6 1.3929(13) . ?
C2 C3 1.3939(13) . ?
C2 H2 0.95 . ?
C3 C4 1.3980(13) . ?
C4 C5 1.3821(15) . ?
C4 H4 0.95 . ?
C5 C6 1.3869(15) . ?
C5 H5 0.95 . ?
C6 H6 0.95 . ?
C7 C8 1.3833(13) . ?
C7 H7 0.95 . ?
C8 C9 1.3914(13) . ?
C8 H8 0.95 . ?
C9 C19 1.356(12) . ?
C9 C10 1.3923(14) . ?
C9 C12B 1.397(19) . ?
C9 C12A 1.503(3) . ?
C10 C11 1.3797(14) . ?
C10 H10 0.95 . ?
C11 H11 0.95 . ?
C12A C13A 1.344(5) . ?
C12A H12A 0.95 . ?
C13A C14A 1.500(3) . ?
C13A H13A 0.95 . ?
C12B C13B 1.254(19) . ?
C12B H12B 0.95 . ?
C13B C14B 1.394(19) . ?
C13B H13B 0.95 . ?
C14A C15A 1.39 . ?
C14A C18A 1.39 . ?
C15A C16A 1.39 . ?
C15A H15A 0.95 . ?
C16A N2A 1.39 . ?
C16A H16A 0.95 . ?
N2A C17A 1.39 . ?
C17A C18A 1.39 . ?
C17A H17A 0.95 . ?
C18A H18A 0.95 . ?
C14B C20 1.357(12) . ?
C14B C18B 1.362(9) . ?
C14B C15B 1.407(9) . ?
C15B C16B 1.355(9) . ?
C15B H15B 0.95 . ?
C16B N2B 1.206(9) . ?
C16B C17B 1.929(15) . ?
C16B H16B 0.95 . ?
N2B C17B 1.208(8) . ?
C17B C18B 1.373(7) . ?
C17B H17B 0.95 . ?
C18B H18B 0.95 . ?
C19 C20 1.183(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 0.84 1.9 2.7396(10) 175.6 1_556 yes
O2 H2A N2A^a 0.84 1.94 2.78(2) 177.2 2_666 yes
O2 H2A N2B^b 0.84 1.83 2.668(9) 176.9 2_666 yes
