#------------------------------------------------------------------------------
#$Date: 2020-06-06 04:19:29 +0300 (Sat, 06 Jun 2020) $
#$Revision: 252960 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/82/1558230.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_1558230
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            'C17.57 H15.57 N2.43 O2'
_chemical_formula_weight         292.75
_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             2020-03-10T15:55:32-00:00
_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                92.9895(18)
_cell_angle_beta                 107.0934(13)
_cell_angle_gamma                114.3019(13)
_cell_formula_units_Z            2
_cell_length_a                   8.05644(11)
_cell_length_b                   9.86768(17)
_cell_length_c                   10.88249(16)
_cell_measurement_reflns_used    16051
_cell_measurement_temperature    210(2)
_cell_measurement_theta_max      76.965
_cell_measurement_theta_min      4.306
_cell_volume                     738.62(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      N~2~
_diffrn_ambient_temperature      210(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.968
_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      0.0007709
_diffrn_orient_matrix_UB_12      0.0471249
_diffrn_orient_matrix_UB_13      -0.148165
_diffrn_orient_matrix_UB_21      -0.073349
_diffrn_orient_matrix_UB_22      0.168272
_diffrn_orient_matrix_UB_23      0.0096655
_diffrn_orient_matrix_UB_31      0.200578
_diffrn_orient_matrix_UB_32      -0.0037922
_diffrn_orient_matrix_UB_33      -0.0281225
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_av_unetI/netI     0.0477
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            27429
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         77.205
_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    0.709
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.522
_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    1.316
_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         0.178
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.0041(9)
_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   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         3036
_refine_ls_number_restraints     306
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0393
_refine_ls_R_factor_gt           0.0364
_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)+(0.0616P)²+0.0829P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1055
_refine_ls_wR_factor_ref         0.1084
_reflns_Friedel_coverage         0
_reflns_number_gt                2761
_reflns_number_total             3036
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc02795b2.cif
_cod_data_source_block           A25_BE75_210
_cod_database_code               1558230
_shelx_estimated_absorpt_t_min   0.857
_shelx_estimated_absorpt_t_max   0.942
_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 0.16572(11) 0.15772(9) 0.30656(7) 0.0437(2) Uani 1 1 d . . . . .
H1 H 0.198664 0.185478 0.386917 0.066 Uiso 1 1 calc R U . . .
O2 O 0.82386(12) 0.22858(10) 0.43224(8) 0.0498(2) Uani 1 1 d . . . . .
H2A H 0.828147 0.265696 0.503989 0.075 Uiso 1 1 calc R U . . .
N1 N 0.26109(14) 0.24720(11) 0.57132(9) 0.0449(2) Uani 1 1 d . . . . .
N2A N 0.233(4) 0.379(2) 0.9421(19) 0.037(2) Uani 0.196(3) 1 d D U P A 1
N3A N 0.269(4) 0.507(2) 0.993(2) 0.040(3) Uani 0.196(3) 1 d D U P A 1
C17 C 0.2139(11) 0.3786(7) 0.9340(5) 0.0363(8) Uani 0.786(3) 1 d D U P A 2
H17 H 0.155999 0.300224 0.975521 0.044 Uiso 0.786(3) 1 calc DR U P A 2
C18 C 0.2656(12) 0.5199(7) 0.9871(6) 0.0348(6) Uani 0.786(3) 1 d D U P A 2
H18 H 0.324663 0.598658 0.94629 0.042 Uiso 0.786(3) 1 calc R U P A 2
N2B N 0.251(8) 0.457(7) 0.919(5) 0.038(3) Uani 0.0179(16) 1 d D U P A 3
N3B N 0.185(7) 0.408(6) 1.006(4) 0.039(3) Uani 0.0179(16) 1 d D U P A 3
N4 N 0.17513(13) 0.65115(11) 1.33254(8) 0.0417(2) Uani 1 1 d . . . . .
C1 C 0.31681(16) 0.15417(10) 0.27792(10) 0.0362(2) Uani 1 1 d . . . . .
C2 C 0.49448(15) 0.19204(11) 0.37432(9) 0.0363(2) Uani 1 1 d . . . . .
H2 H 0.511742 0.219819 0.462776 0.044 Uiso 1 1 calc R U . . .
C3 C 0.64730(16) 0.18922(11) 0.34110(10) 0.0386(2) Uani 1 1 d . . . . .
C4 C 0.62086(18) 0.14526(12) 0.20983(11) 0.0439(3) Uani 1 1 d . . . . .
H4 H 0.722508 0.141575 0.186365 0.053 Uiso 1 1 calc R U . . .
C5 C 0.44281(19) 0.10734(12) 0.11523(10) 0.0454(3) Uani 1 1 d . . . . .
H5 H 0.424917 0.078395 0.026833 0.054 Uiso 1 1 calc R U . . .
C6 C 0.28991(17) 0.11071(12) 0.14672(10) 0.0424(3) Uani 1 1 d . . . . .
H6 H 0.169813 0.084114 0.080739 0.051 Uiso 1 1 calc R U . . .
C7 C 0.32241(17) 0.39358(13) 0.62046(11) 0.0451(3) Uani 1 1 d . . . . .
H7 H 0.371057 0.465612 0.570975 0.054 Uiso 1 1 calc R U . . .
C8 C 0.31841(17) 0.44479(12) 0.73915(11) 0.0420(3) Uani 1 1 d . . . . .
H8 H 0.365423 0.549085 0.769973 0.05 Uiso 1 1 calc R U . . .
C9 C 0.24343(15) 0.33937(12) 0.81305(10) 0.0364(2) Uani 1 1 d D . . . .
C10 C 0.18345(16) 0.18756(12) 0.76343(11) 0.0423(3) Uani 1 1 d . . . . .
H10 H 0.135128 0.1129 0.810938 0.051 Uiso 1 1 calc R U . . .
C11 C 0.19528(17) 0.14719(13) 0.64417(11) 0.0450(3) Uani 1 1 d . . . . .
H11 H 0.154996 0.044138 0.612637 0.054 Uiso 1 1 calc R U . . .
C12 C 0.23360(14) 0.55764(12) 1.10759(10) 0.0358(2) Uani 1 1 d D . . . .
C13 C 0.28711(16) 0.70879(12) 1.15259(11) 0.0423(3) Uani 1 1 d . . . . .
H13 H 0.344215 0.783016 1.107368 0.051 Uiso 1 1 calc R U . . .
C14 C 0.25637(17) 0.75000(12) 1.26384(11) 0.0447(3) Uani 1 1 d . . . . .
H14 H 0.294737 0.853289 1.2928 0.054 Uiso 1 1 calc R U . . .
C15 C 0.12201(16) 0.50469(13) 1.28921(10) 0.0408(2) Uani 1 1 d . . . . .
H15 H 0.063717 0.433129 1.336001 0.049 Uiso 1 1 calc R U . . .
C16 C 0.14857(16) 0.45349(12) 1.17926(10) 0.0401(2) Uani 1 1 d . . . . .
H16 H 0.109806 0.349614 1.152936 0.048 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 0 -6 0.0337
3 6 0 0.0565
-2 0 6 0.0536
1 6 1 0.0529
0 -6 -1 0.0564
5 2 3 0.1012
-5 -5 -1 0.093
0 6 4 0.0506
0 0 7 0.0473
-4 2 0 0.1051
1 -4 3 0.0582
-3 -4 3 0.0674
-1 -1 -7 0.0394
0 -3 5 0.0488
0 3 6 0.0455
-1 -4 -6 0.0412
-4 -4 -5 0.0836
-1 -6 -4 0.0452
3 6 4 0.0661
-3 3 -3 0.0956
-5 -2 -3 0.1148
4 5 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 117.00(9) . . ?
N3A N2A C9 124.7(18) . . ?
N2A N3A C12 130.5(19) . . ?
C18 C17 C9 122.6(5) . . ?
C18 C17 H17 118.7 . . ?
C9 C17 H17 118.7 . . ?
C17 C18 C12 122.1(5) . . ?
C17 C18 H18 118.9 . . ?
C12 C18 H18 118.9 . . ?
N3B N2B C9 117(5) . . ?
N2B N3B C12 106(5) . . ?
C14 N4 C15 117.04(9) . . ?
O1 C1 C2 122.10(9) . . ?
O1 C1 C6 118.05(10) . . ?
C2 C1 C6 119.84(10) . . ?
C1 C2 C3 120.53(9) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
O2 C3 C2 122.14(9) . . ?
O2 C3 C4 118.03(10) . . ?
C2 C3 C4 119.83(10) . . ?
C5 C4 C3 118.85(11) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C4 C5 C6 121.95(10) . . ?
C4 C5 H5 119 . . ?
C6 C5 H5 119 . . ?
C5 C6 C1 118.99(10) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
N1 C7 C8 123.87(10) . . ?
N1 C7 H7 118.1 . . ?
C8 C7 H7 118.1 . . ?
C7 C8 C9 118.95(10) . . ?
C7 C8 H8 120.5 . . ?
C9 C8 H8 120.5 . . ?
C10 C9 C8 117.22(10) . . ?
C10 C9 C17 118.8(3) . . ?
C8 C9 C17 123.8(3) . . ?
C10 C9 N2A 118.2(8) . . ?
C8 C9 N2A 124.5(8) . . ?
C10 C9 N2B 147.2(18) . . ?
C8 C9 N2B 95.2(18) . . ?
C11 C10 C9 119.65(10) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
N1 C11 C10 123.25(10) . . ?
N1 C11 H11 118.4 . . ?
C10 C11 H11 118.4 . . ?
C13 C12 C16 116.97(10) . . ?
C13 C12 N3A 122.5(9) . . ?
C16 C12 N3A 120.5(9) . . ?
C13 C12 C18 117.5(3) . . ?
C16 C12 C18 125.5(3) . . ?
C13 C12 N3B 157.7(15) . . ?
C16 C12 N3B 84.8(15) . . ?
C14 C13 C12 119.82(10) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
N4 C14 C13 123.48(10) . . ?
N4 C14 H14 118.3 . . ?
C13 C14 H14 118.3 . . ?
N4 C15 C16 123.34(10) . . ?
N4 C15 H15 118.3 . . ?
C16 C15 H15 118.3 . . ?
C15 C16 C12 119.35(10) . . ?
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 1.3554(13) . ?
O1 H1 0.83 . ?
O2 C3 1.3541(13) . ?
O2 H2A 0.83 . ?
N1 C11 1.3348(15) . ?
N1 C7 1.3391(15) . ?
N2A N3A 1.234(10) . ?
N2A C9 1.472(16) . ?
N3A C12 1.466(17) . ?
C17 C18 1.322(4) . ?
C17 C9 1.465(5) . ?
C17 H17 0.94 . ?
C18 C12 1.467(5) . ?
C18 H18 0.94 . ?
N2B N3B 1.242(10) . ?
N2B C9 1.56(6) . ?
N3B C12 1.63(5) . ?
N4 C14 1.3330(15) . ?
N4 C15 1.3399(14) . ?
C1 C2 1.3875(15) . ?
C1 C6 1.3953(14) . ?
C2 C3 1.3915(15) . ?
C2 H2 0.94 . ?
C3 C4 1.3981(14) . ?
C4 C5 1.3811(17) . ?
C4 H4 0.94 . ?
C5 C6 1.3845(17) . ?
C5 H5 0.94 . ?
C6 H6 0.94 . ?
C7 C8 1.3765(15) . ?
C7 H7 0.94 . ?
C8 C9 1.3962(15) . ?
C8 H8 0.94 . ?
C9 C10 1.3912(15) . ?
C10 C11 1.3792(15) . ?
C10 H10 0.94 . ?
C11 H11 0.94 . ?
C12 C13 1.3859(15) . ?
C12 C16 1.3971(15) . ?
C13 C14 1.3785(16) . ?
C13 H13 0.94 . ?
C14 H14 0.94 . ?
C15 C16 1.3817(15) . ?
C15 H15 0.94 . ?
C16 H16 0.94 . ?
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 2.7470(12) 177 . yes
O2 H2A N4 0.83 1.93 2.7612(12) 177.3 2_667 yes
