#------------------------------------------------------------------------------
#$Date: 2020-06-06 04:19:29 +0300 (Sat, 06 Jun 2020) $
#$Revision: 252960 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/82/1558234.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_1558234
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            'C17.04 H15.04 N2.96 O2'
_chemical_formula_weight         293.28
_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             2020-03-05T13:02:21-00:00
_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                93.5909(14)
_cell_angle_beta                 106.7035(16)
_cell_angle_gamma                113.9933(18)
_cell_formula_units_Z            2
_cell_length_a                   8.04836(15)
_cell_length_b                   9.83877(18)
_cell_length_c                   10.88786(18)
_cell_measurement_reflns_used    11392
_cell_measurement_temperature    250(2)
_cell_measurement_theta_max      76.456
_cell_measurement_theta_min      4.308
_cell_volume                     738.39(3)
_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      250(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.947
_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      0.1316136
_diffrn_orient_matrix_UB_12      -0.0768229
_diffrn_orient_matrix_UB_13      0.0519159
_diffrn_orient_matrix_UB_21      0.0243496
_diffrn_orient_matrix_UB_22      0.0591271
_diffrn_orient_matrix_UB_23      0.1415476
_diffrn_orient_matrix_UB_31      -0.1784411
_diffrn_orient_matrix_UB_32      -0.1458328
_diffrn_orient_matrix_UB_33      -0.0071389
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0503
_diffrn_reflns_av_unetI/netI     0.061
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_limit_h_max       10
_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            21652
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         77.151
_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    0.721
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.501
_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    1.319
_exptl_crystal_description       irregular
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.269
_exptl_crystal_size_mid          0.156
_exptl_crystal_size_min          0.102
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.139
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       0.0054(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   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         2966
_refine_ls_number_restraints     306
_refine_ls_restrained_S_all      0.998
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0387
_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)+(0.0559P)²+0.0995P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1032
_refine_ls_wR_factor_ref         0.1148
_reflns_Friedel_coverage         0
_reflns_number_gt                2431
_reflns_number_total             2966
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc02795b2.cif
_cod_data_source_block           A50_BE50_250
_cod_database_code               1558234
_shelx_estimated_absorpt_t_min   0.869
_shelx_estimated_absorpt_t_max   0.929
_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 0.16581(14) 0.15789(12) 0.30922(9) 0.0558(3) Uani 1 1 d . . . . .
H1 H 0.197668 0.183425 0.389776 0.084 Uiso 1 1 calc R U . . .
O2 O 0.82176(15) 0.22581(14) 0.43261(10) 0.0640(3) Uani 1 1 d . . . . .
H2A H 0.825245 0.262032 0.504752 0.096 Uiso 1 1 calc R U . . .
N1 N 0.26027(17) 0.24807(15) 0.57516(11) 0.0549(3) Uani 1 1 d . . . . .
N2A N 0.222(2) 0.3797(15) 0.9439(12) 0.0474(19) Uani 0.422(3) 1 d D U P A 1
N3A N 0.270(2) 0.5136(15) 0.9882(14) 0.049(2) Uani 0.422(3) 1 d D U P A 1
C17 C 0.212(2) 0.3769(14) 0.9343(12) 0.0455(16) Uani 0.519(3) 1 d D U P A 2
H17 H 0.155733 0.298651 0.976019 0.055 Uiso 0.519(3) 1 calc DR U P A 2
C18 C 0.263(2) 0.5185(14) 0.9844(13) 0.0434(14) Uani 0.519(3) 1 d D U P A 2
H18 H 0.318208 0.596656 0.942284 0.052 Uiso 0.519(3) 1 calc R U P A 2
N2B N 0.272(3) 0.468(3) 0.923(2) 0.048(3) Uani 0.059(2) 1 d D U P A 3
N3B N 0.189(3) 0.404(3) 0.998(2) 0.049(3) Uani 0.059(2) 1 d D U P A 3
N4 N 0.17652(16) 0.65066(14) 1.33047(11) 0.0521(3) Uani 1 1 d . . . . .
C1 C 0.3171(2) 0.15398(14) 0.27965(12) 0.0447(3) Uani 1 1 d . . . . .
C2 C 0.49337(19) 0.19047(14) 0.37567(12) 0.0453(3) Uani 1 1 d . . . . .
H2 H 0.509813 0.217322 0.464241 0.054 Uiso 1 1 calc R U . . .
C3 C 0.6463(2) 0.18759(15) 0.34175(12) 0.0478(3) Uani 1 1 d . . . . .
C4 C 0.6206(2) 0.14478(16) 0.21084(14) 0.0544(4) Uani 1 1 d . . . . .
H4 H 0.72197 0.140612 0.186928 0.065 Uiso 1 1 calc R U . . .
C5 C 0.4441(2) 0.10857(16) 0.11673(13) 0.0568(4) Uani 1 1 d . . . . .
H5 H 0.42685 0.080312 0.028215 0.068 Uiso 1 1 calc R U . . .
C6 C 0.2918(2) 0.11263(16) 0.14879(13) 0.0531(3) Uani 1 1 d . . . . .
H6 H 0.17276 0.087764 0.082998 0.064 Uiso 1 1 calc R U . . .
C7 C 0.3222(2) 0.39480(18) 0.62451(14) 0.0566(4) Uani 1 1 d . . . . .
H7 H 0.370998 0.466439 0.575155 0.068 Uiso 1 1 calc R U . . .
C8 C 0.3186(2) 0.44708(17) 0.74369(14) 0.0541(3) Uani 1 1 d . . . . .
H8 H 0.365793 0.551676 0.775117 0.065 Uiso 1 1 calc R U . . .
C9 C 0.24376(19) 0.34205(16) 0.81628(12) 0.0465(3) Uani 1 1 d D . . . .
C10 C 0.1832(2) 0.19042(17) 0.76720(14) 0.0533(3) Uani 1 1 d . . . . .
H10 H 0.134705 0.116318 0.814732 0.064 Uiso 1 1 calc R U . . .
C11 C 0.1946(2) 0.14913(17) 0.64800(14) 0.0554(4) Uani 1 1 d . . . . .
H11 H 0.153952 0.045622 0.616229 0.067 Uiso 1 1 calc R U . . .
C12 C 0.23217(19) 0.55437(16) 1.10578(12) 0.0472(3) Uani 1 1 d D . . . .
C13 C 0.2861(2) 0.70527(17) 1.14981(14) 0.0555(4) Uani 1 1 d . . . . .
H13 H 0.342513 0.778606 1.104035 0.067 Uiso 1 1 calc R U . . .
C14 C 0.2569(2) 0.74783(17) 1.26132(14) 0.0570(4) Uani 1 1 d . . . . .
H14 H 0.295921 0.851644 1.290412 0.068 Uiso 1 1 calc R U . . .
C15 C 0.1228(2) 0.50386(17) 1.28745(13) 0.0522(3) Uani 1 1 d . . . . .
H15 H 0.06529 0.433184 1.334776 0.063 Uiso 1 1 calc R U . . .
C16 C 0.1478(2) 0.45064(16) 1.17659(13) 0.0521(3) Uani 1 1 d . . . . .
H16 H 0.108352 0.346341 1.149694 0.063 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
-4 -2 1 0.0681
3 3 -3 0.0873
0 6 -2 0.0863
4 1 -1 0.0905
-1 -2 -4 0.0457
0 -6 2 0.0494
2 2 -7 0.0731
-1 0 7 0.036
-2 1 -5 0.0681
0 4 -6 0.0553
3 0 4 0.092
4 -5 -3 0.1384
-3 6 2 0.1189
1 -3 -5 0.0535
0 0 -7 0.0505
-3 6 -2 0.1171
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 116.92(12) . . ?
N3A N2A C9 118.3(11) . . ?
N2A N3A C12 120.3(12) . . ?
C18 C17 C9 119.8(10) . . ?
C18 C17 H17 120.1 . . ?
C9 C17 H17 120.1 . . ?
C17 C18 C12 119.8(11) . . ?
C17 C18 H18 120.1 . . ?
C12 C18 H18 120.1 . . ?
N3B N2B C9 107(2) . . ?
N2B N3B C12 101(2) . . ?
C14 N4 C15 117.02(12) . . ?
O1 C1 C2 121.91(11) . . ?
O1 C1 C6 118.18(12) . . ?
C2 C1 C6 119.91(12) . . ?
C1 C2 C3 120.41(11) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
O2 C3 C4 118.23(12) . . ?
O2 C3 C2 122.04(11) . . ?
C4 C3 C2 119.73(13) . . ?
C5 C4 C3 119.01(13) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C5 C6 121.89(12) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C5 C6 C1 119.04(13) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
N1 C7 C8 123.73(14) . . ?
N1 C7 H7 118.1 . . ?
C8 C7 H7 118.1 . . ?
C7 C8 C9 118.59(14) . . ?
C7 C8 H8 120.7 . . ?
C9 C8 H8 120.7 . . ?
C10 C9 C8 118.02(12) . . ?
C10 C9 C17 116.8(5) . . ?
C8 C9 C17 125.1(5) . . ?
C10 C9 N2A 116.9(5) . . ?
C8 C9 N2A 125.1(5) . . ?
C10 C9 N2B 150.4(8) . . ?
C8 C9 N2B 91.6(8) . . ?
C11 C10 C9 119.23(14) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
N1 C11 C10 123.47(14) . . ?
N1 C11 H11 118.3 . . ?
C10 C11 H11 118.3 . . ?
C13 C12 C16 117.89(12) . . ?
C13 C12 C18 115.8(5) . . ?
C16 C12 C18 126.3(5) . . ?
C13 C12 N3A 117.8(6) . . ?
C16 C12 N3A 124.3(6) . . ?
C13 C12 N3B 154.9(6) . . ?
C16 C12 N3B 86.9(6) . . ?
C14 C13 C12 119.34(14) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
N4 C14 C13 123.76(14) . . ?
N4 C14 H14 118.1 . . ?
C13 C14 H14 118.1 . . ?
N4 C15 C16 123.23(13) . . ?
N4 C15 H15 118.4 . . ?
C16 C15 H15 118.4 . . ?
C15 C16 C12 118.75(13) . . ?
C15 C16 H16 120.6 . . ?
C12 C16 H16 120.6 . . ?
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 1.3603(16) . ?
O1 H1 0.83 . ?
O2 C3 1.3535(17) . ?
O2 H2A 0.83 . ?
N1 C11 1.332(2) . ?
N1 C7 1.3360(19) . ?
N2A N3A 1.231(8) . ?
N2A C9 1.493(11) . ?
N3A C12 1.465(12) . ?
C17 C18 1.313(7) . ?
C17 C9 1.426(11) . ?
C17 H17 0.94 . ?
C18 C12 1.459(10) . ?
C18 H18 0.94 . ?
N2B N3B 1.241(10) . ?
N2B C9 1.54(2) . ?
N3B C12 1.68(2) . ?
N4 C14 1.329(2) . ?
N4 C15 1.3356(18) . ?
C1 C2 1.3856(18) . ?
C1 C6 1.3892(18) . ?
C2 C3 1.3934(18) . ?
C2 H2 0.94 . ?
C3 C4 1.3912(18) . ?
C4 C5 1.379(2) . ?
C4 H4 0.94 . ?
C5 C6 1.382(2) . ?
C5 H5 0.94 . ?
C6 H6 0.94 . ?
C7 C8 1.378(2) . ?
C7 H7 0.94 . ?
C8 C9 1.387(2) . ?
C8 H8 0.94 . ?
C9 C10 1.3812(19) . ?
C10 C11 1.3751(19) . ?
C10 H10 0.94 . ?
C11 H11 0.94 . ?
C12 C13 1.375(2) . ?
C12 C16 1.390(2) . ?
C13 C14 1.373(2) . ?
C13 H13 0.94 . ?
C14 H14 0.94 . ?
C15 C16 1.3845(19) . ?
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 1.93 2.7592(15) 176.4 . yes
O2 H2A N4 0.83 1.95 2.7757(14) 177.3 2_667 yes
