#------------------------------------------------------------------------------
#$Date: 2020-06-06 04:19:29 +0300 (Sat, 06 Jun 2020) $
#$Revision: 252960 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/82/1558237.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_1558237
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            'C17.54 H15.54 N2.46 O2'
_chemical_formula_weight         292.78
_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             2020-03-10T15:59:10-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2020-04-07 deposited with the CCDC.	2020-06-05 downloaded from the CCDC.
;
_cell_angle_alpha                93.3530(10)
_cell_angle_beta                 107.0207(13)
_cell_angle_gamma                114.1614(13)
_cell_formula_units_Z            2
_cell_length_a                   8.13099(12)
_cell_length_b                   9.90773(12)
_cell_length_c                   10.90319(14)
_cell_measurement_reflns_used    13314
_cell_measurement_temperature    290(2)
_cell_measurement_theta_max      76.674
_cell_measurement_theta_min      4.305
_cell_volume                     750.13(2)
_computing_cell_refinement       'CrysAlisPro 1.171.40.70a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.70a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.70a (Rigaku OD, 2020)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      290(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.96
_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      -0.0494613
_diffrn_orient_matrix_UB_12      -0.0484487
_diffrn_orient_matrix_UB_13      -0.1481812
_diffrn_orient_matrix_UB_21      -0.0934682
_diffrn_orient_matrix_UB_22      -0.1671676
_diffrn_orient_matrix_UB_23      0.0101577
_diffrn_orient_matrix_UB_31      -0.1945979
_diffrn_orient_matrix_UB_32      0.0040927
_diffrn_orient_matrix_UB_33      -0.0269431
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_av_unetI/netI     0.0498
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.96
_diffrn_reflns_limit_h_max       8
_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            26809
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.96
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         77.306
_diffrn_reflns_theta_min         4.332
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.699
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.651
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
        CrysAlisPro 1.171.40.70a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
                        a multifaceted crystal model
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_description       irregular
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.224
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.085
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.03
_refine_ls_extinction_coef       0.0039(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   0.991
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         3064
_refine_ls_number_restraints     306
_refine_ls_restrained_S_all      0.948
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0398
_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)+(0.0588P)²+0.1041P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1081
_refine_ls_wR_factor_ref         0.1131
_reflns_Friedel_coverage         0
_reflns_number_gt                2598
_reflns_number_total             3064
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc02795b2.cif
_cod_data_source_block           A25_BE75_290
_cod_original_cell_volume        750.133(19)
_cod_database_code               1558237
_shelx_estimated_absorpt_t_min   0.859
_shelx_estimated_absorpt_t_max   0.943
_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 0.16725(13) 0.15419(11) 0.30654(9) 0.0638(3) Uani 1 1 d . . . . .
H1 H 0.199338 0.181103 0.385938 0.096 Uiso 1 1 calc R U . . .
O2 O 0.81968(14) 0.22732(13) 0.43102(9) 0.0729(3) Uani 1 1 d . . . . .
H2A H 0.823285 0.262306 0.50234 0.109 Uiso 1 1 calc R U . . .
N1 N 0.26014(16) 0.24608(14) 0.57109(10) 0.0631(3) Uani 1 1 d . . . . .
N2A N 0.243(5) 0.386(3) 0.941(2) 0.049(3) Uani 0.144(3) 1 d D U P A 1
N3A N 0.276(6) 0.511(3) 0.997(3) 0.054(3) Uani 0.144(3) 1 d D U P A 1
C17 C 0.2139(9) 0.3776(7) 0.9339(5) 0.0517(10) Uani 0.771(3) 1 d D U P A 2
H17 H 0.158665 0.299849 0.974617 0.062 Uiso 0.771(3) 1 calc DR U P A 2
C18 C 0.2630(12) 0.5171(7) 0.9863(6) 0.0500(8) Uani 0.771(3) 1 d D U P A 2
H18 H 0.318707 0.594434 0.945393 0.06 Uiso 0.771(3) 1 calc R U P A 2
N2B N 0.2705(19) 0.4654(17) 0.9190(12) 0.054(2) Uani 0.085(2) 1 d D U P A 3
N3B N 0.1978(19) 0.4111(16) 1.0015(13) 0.056(2) Uani 0.085(2) 1 d D U P A 3
N4 N 0.17718(15) 0.65107(13) 1.33265(10) 0.0588(3) Uani 1 1 d . . . . .
C1 C 0.31748(18) 0.15164(12) 0.27761(11) 0.0510(3) Uani 1 1 d . . . . .
C2 C 0.49310(18) 0.18962(13) 0.37364(11) 0.0515(3) Uani 1 1 d . . . . .
H2 H 0.509811 0.216523 0.461165 0.062 Uiso 1 1 calc R U . . .
C3 C 0.64460(19) 0.18783(14) 0.34023(12) 0.0548(3) Uani 1 1 d . . . . .
C4 C 0.6187(2) 0.14484(15) 0.20937(13) 0.0625(3) Uani 1 1 d . . . . .
H4 H 0.718529 0.141893 0.185967 0.075 Uiso 1 1 calc R U . . .
C5 C 0.4429(2) 0.10684(15) 0.11542(12) 0.0650(4) Uani 1 1 d . . . . .
H5 H 0.425596 0.078729 0.02796 0.078 Uiso 1 1 calc R U . . .
C6 C 0.2916(2) 0.10913(14) 0.14694(12) 0.0601(3) Uani 1 1 d . . . . .
H6 H 0.173838 0.082612 0.081697 0.072 Uiso 1 1 calc R U . . .
C7 C 0.3216(2) 0.39226(16) 0.61965(13) 0.0648(3) Uani 1 1 d . . . . .
H7 H 0.369331 0.462391 0.570519 0.078 Uiso 1 1 calc R U . . .
C8 C 0.3182(2) 0.44467(15) 0.73785(13) 0.0617(3) Uani 1 1 d . . . . .
H8 H 0.364554 0.547679 0.76795 0.074 Uiso 1 1 calc R U . . .
C9 C 0.24456(18) 0.34148(15) 0.81191(11) 0.0538(3) Uani 1 1 d D . . . .
C10 C 0.1853(2) 0.19123(15) 0.76319(13) 0.0615(3) Uani 1 1 d . . . . .
H10 H 0.13847 0.11869 0.810717 0.074 Uiso 1 1 calc R U . . .
C11 C 0.1953(2) 0.14883(16) 0.64474(13) 0.0641(3) Uani 1 1 d . . . . .
H11 H 0.154605 0.046799 0.614159 0.077 Uiso 1 1 calc R U . . .
C12 C 0.23265(17) 0.55540(15) 1.10815(11) 0.0544(3) Uani 1 1 d D . . . .
C13 C 0.2855(2) 0.70449(15) 1.15269(13) 0.0627(3) Uani 1 1 d . . . . .
H13 H 0.34102 0.776895 1.107678 0.075 Uiso 1 1 calc R U . . .
C14 C 0.2569(2) 0.74700(15) 1.26317(13) 0.0645(3) Uani 1 1 d . . . . .
H14 H 0.295525 0.849174 1.291395 0.077 Uiso 1 1 calc R U . . .
C15 C 0.12361(19) 0.50527(15) 1.28989(12) 0.0590(3) Uani 1 1 d . . . . .
H15 H 0.066553 0.435588 1.336355 0.071 Uiso 1 1 calc R U . . .
C16 C 0.1489(2) 0.45289(15) 1.17976(13) 0.0596(3) Uani 1 1 d . . . . .
H16 H 0.110419 0.350336 1.153748 0.072 Uiso 1 1 calc DR U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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
-1 1 -6 0.0337
-3 -3 0 0.0565
2 -1 6 0.0536
-1 -5 1 0.0529
0 6 -1 0.0564
-5 3 3 0.1012
5 0 -1 0.093
0 -5 4 0.0506
0 0 7 0.0473
4 -6 0 0.1051
-1 5 3 0.0582
3 0 3 0.0674
1 0 -7 0.0394
0 3 5 0.0488
0 -3 6 0.0455
1 3 -7 0.0412
4 0 -6 0.0836
1 5 -4 0.0452
-3 -3 4 0.0661
3 -6 -3 0.0956
5 -3 -3 0.1148
-5 -1 1 0.0716
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 . . ?
C11 N1 C7 116.60(11) . . ?
N3A N2A C9 130(2) . . ?
N2A N3A C12 132(2) . . ?
C18 C17 C9 121.3(5) . . ?
C18 C17 H17 119.4 . . ?
C9 C17 H17 119.4 . . ?
C17 C18 C12 122.1(5) . . ?
C17 C18 H18 119 . . ?
C12 C18 H18 119 . . ?
N3B N2B C9 112.2(14) . . ?
N2B N3B C12 107.0(12) . . ?
C14 N4 C15 116.66(11) . . ?
O1 C1 C2 122.06(10) . . ?
O1 C1 C6 118.18(12) . . ?
C2 C1 C6 119.76(12) . . ?
C1 C2 C3 120.48(11) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
O2 C3 C2 122.23(10) . . ?
O2 C3 C4 117.95(12) . . ?
C2 C3 C4 119.82(12) . . ?
C5 C4 C3 118.86(13) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C4 C5 C6 122.01(11) . . ?
C4 C5 H5 119 . . ?
C6 C5 H5 119 . . ?
C5 C6 C1 119.06(13) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
N1 C7 C8 123.77(13) . . ?
N1 C7 H7 118.1 . . ?
C8 C7 H7 118.1 . . ?
C7 C8 C9 119.04(13) . . ?
C7 C8 H8 120.5 . . ?
C9 C8 H8 120.5 . . ?
C10 C9 C8 117.14(12) . . ?
C10 C9 N2A 119.6(12) . . ?
C8 C9 N2A 123.1(12) . . ?
C10 C9 C17 117.1(3) . . ?
C8 C9 C17 125.7(3) . . ?
C10 C9 N2B 149.7(5) . . ?
C8 C9 N2B 93.1(5) . . ?
C11 C10 C9 119.97(13) . . ?
C11 C10 H10 120 . . ?
C9 C10 H10 120 . . ?
N1 C11 C10 123.44(13) . . ?
N1 C11 H11 118.3 . . ?
C10 C11 H11 118.3 . . ?
C13 C12 C16 116.89(12) . . ?
C13 C12 N3A 120.4(12) . . ?
C16 C12 N3A 122.6(12) . . ?
C13 C12 C18 117.2(3) . . ?
C16 C12 C18 125.9(3) . . ?
C13 C12 N3B 154.2(4) . . ?
C16 C12 N3B 88.8(4) . . ?
C14 C13 C12 120.10(13) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
N4 C14 C13 123.91(13) . . ?
N4 C14 H14 118 . . ?
C13 C14 H14 118 . . ?
N4 C15 C16 123.12(12) . . ?
N4 C15 H15 118.4 . . ?
C16 C15 H15 118.4 . . ?
C15 C16 C12 119.31(12) . . ?
C15 C16 H16 120.3 . . ?
C12 C16 H16 120.3 . . ?
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 1.3572(15) . ?
O1 H1 0.82 . ?
O2 C3 1.3540(16) . ?
O2 H2A 0.82 . ?
N1 C11 1.3319(18) . ?
N1 C7 1.3382(18) . ?
N2A N3A 1.234(10) . ?
N2A C9 1.454(19) . ?
N3A C12 1.444(19) . ?
C17 C18 1.311(3) . ?
C17 C9 1.474(5) . ?
C17 H17 0.93 . ?
C18 C12 1.476(4) . ?
C18 H18 0.93 . ?
N2B N3B 1.247(10) . ?
N2B C9 1.547(14) . ?
N3B C12 1.661(15) . ?
N4 C14 1.3284(18) . ?
N4 C15 1.3346(17) . ?
C1 C2 1.3841(17) . ?
C1 C6 1.3904(16) . ?
C2 C3 1.3893(18) . ?
C2 H2 0.93 . ?
C3 C4 1.3932(17) . ?
C4 C5 1.375(2) . ?
C4 H4 0.93 . ?
C5 C6 1.380(2) . ?
C5 H5 0.93 . ?
C6 H6 0.93 . ?
C7 C8 1.3729(19) . ?
C7 H7 0.93 . ?
C8 C9 1.3909(19) . ?
C8 H8 0.93 . ?
C9 C10 1.3786(18) . ?
C10 C11 1.3701(18) . ?
C10 H10 0.93 . ?
C11 H11 0.93 . ?
C12 C13 1.3699(19) . ?
C12 C16 1.3938(19) . ?
C13 C14 1.3667(19) . ?
C13 H13 0.93 . ?
C14 H14 0.93 . ?
C15 C16 1.3829(18) . ?
C15 H15 0.93 . ?
C16 H16 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
_geom_hbond_publ_flag
O1 H1 N1 0.82 1.93 2.7520(14) 176.3 . yes
O2 H2A N4 0.82 1.95 2.7685(13) 177.2 2_667 yes
