#------------------------------------------------------------------------------
#$Date: 2020-06-06 04:19:29 +0300 (Sat, 06 Jun 2020) $
#$Revision: 252960 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/82/1558252.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_1558252
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            'C16.5 H14.5 N3.5 O2'
_chemical_formula_weight         293.82
_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             2020-04-02T13:30:34-00:00
_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                93.5338(16)
_cell_angle_beta                 106.566(2)
_cell_angle_gamma                113.8855(19)
_cell_formula_units_Z            2
_cell_length_a                   7.9561(2)
_cell_length_b                   9.75452(15)
_cell_length_c                   10.8395(2)
_cell_measurement_reflns_used    15572
_cell_measurement_temperature    190(2)
_cell_measurement_theta_max      76.874
_cell_measurement_theta_min      4.321
_cell_volume                     722.05(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      190(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 0.974
_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      -0.0288333
_diffrn_orient_matrix_UB_12      -0.1662221
_diffrn_orient_matrix_UB_13      -0.0021205
_diffrn_orient_matrix_UB_21      -0.1070004
_diffrn_orient_matrix_UB_22      -0.0402865
_diffrn_orient_matrix_UB_23      -0.1496447
_diffrn_orient_matrix_UB_31      0.1960084
_diffrn_orient_matrix_UB_32      0.0430281
_diffrn_orient_matrix_UB_33      -0.0229078
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_unetI/netI     0.0479
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_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            27314
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         77.258
_diffrn_reflns_theta_min         4.345
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.75
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.656
_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 yellow'
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_description       plate
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.219
_exptl_crystal_size_mid          0.132
_exptl_crystal_size_min          0.056
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.0047(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   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         2987
_refine_ls_number_restraints     306
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0372
_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)+(0.0612P)²+0.1131P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1058
_refine_ls_wR_factor_ref         0.1083
_reflns_Friedel_coverage         0
_reflns_number_gt                2731
_reflns_number_total             2987
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc02795b2.cif
_cod_data_source_block           A75_BE25_190
_cod_original_formula_sum        'C16.50 H14.50 N3.50 O2'
_cod_database_code               1558252
_shelx_estimated_absorpt_t_min   0.853
_shelx_estimated_absorpt_t_max   0.959
_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 0.16434(11) 0.16192(9) 0.31149(7) 0.0400(2) Uani 1 1 d . . . . .
H1 H 0.197071 0.188106 0.393281 0.06 Uiso 1 1 calc R U . . .
O2 O 0.82507(12) 0.22415(10) 0.43470(8) 0.0462(2) Uani 1 1 d . . . . .
H2A H 0.829878 0.263654 0.507474 0.069 Uiso 1 1 calc R U . . .
N1 N 0.26106(14) 0.24942(11) 0.57918(9) 0.0404(2) Uani 1 1 d . . . . .
N2A N 0.2137(15) 0.3755(6) 0.9440(7) 0.0349(9) Uani 0.732(3) 1 d D U P A 1
N3A N 0.2687(10) 0.5148(6) 0.9813(4) 0.0330(6) Uani 0.732(3) 1 d D U P A 1
C17 C 0.211(5) 0.382(2) 0.936(3) 0.035(2) Uani 0.248(3) 1 d D U P A 2
H17 H 0.144827 0.299039 0.97292 0.042 Uiso 0.248(3) 1 calc R U P A 2
C18 C 0.262(4) 0.520(2) 0.9998(14) 0.0327(18) Uani 0.248(3) 1 d D U P A 2
H18 H 0.327476 0.60375 0.963494 0.039 Uiso 0.248(3) 1 calc DR U P A 2
N2B N 0.284(7) 0.478(6) 0.927(5) 0.037(3) Uani 0.020(2) 1 d D U P A 3
N3B N 0.181(7) 0.400(6) 0.987(5) 0.037(3) Uani 0.020(2) 1 d D U P A 3
N4 N 0.17507(14) 0.65036(11) 1.32810(9) 0.0387(2) Uani 1 1 d . . . . .
C1 C 0.31665(16) 0.15686(11) 0.28138(10) 0.0336(2) Uani 1 1 d . . . . .
C2 C 0.49397(16) 0.19134(11) 0.37781(10) 0.0342(2) Uani 1 1 d . . . . .
H2 H 0.510438 0.217976 0.467696 0.041 Uiso 1 1 calc R U . . .
C3 C 0.64797(16) 0.18706(12) 0.34333(11) 0.0359(2) Uani 1 1 d . . . . .
C4 C 0.62261(18) 0.14455(13) 0.21168(11) 0.0401(3) Uani 1 1 d . . . . .
H4 H 0.725726 0.139078 0.187358 0.048 Uiso 1 1 calc R U . . .
C5 C 0.44480(19) 0.11050(13) 0.11710(11) 0.0415(3) Uani 1 1 d . . . . .
H5 H 0.427617 0.08244 0.027274 0.05 Uiso 1 1 calc R U . . .
C6 C 0.29098(18) 0.11608(12) 0.14945(11) 0.0394(3) Uani 1 1 d . . . . .
H6 H 0.170165 0.09254 0.082894 0.047 Uiso 1 1 calc R U . . .
C7 C 0.32402(17) 0.39756(13) 0.62955(12) 0.0414(3) Uani 1 1 d . . . . .
H7 H 0.374717 0.470987 0.579914 0.05 Uiso 1 1 calc R U . . .
C8 C 0.31946(17) 0.44956(13) 0.74926(11) 0.0391(3) Uani 1 1 d . . . . .
H8 H 0.367653 0.555858 0.781819 0.047 Uiso 1 1 calc DR U . . .
C9 C 0.24222(15) 0.34176(12) 0.82096(10) 0.0338(2) Uani 1 1 d D . . . .
C10 C 0.17979(17) 0.18812(13) 0.77119(11) 0.0386(3) Uani 1 1 d . . . . .
H10 H 0.129065 0.112161 0.818841 0.046 Uiso 1 1 calc R U . . .
C11 C 0.19288(17) 0.14789(13) 0.65108(11) 0.0402(3) Uani 1 1 d . . . . .
H11 H 0.151313 0.042746 0.617954 0.048 Uiso 1 1 calc R U . . .
C12 C 0.23227(15) 0.55346(13) 1.10289(10) 0.0344(2) Uani 1 1 d D . . . .
C13 C 0.28810(17) 0.70660(13) 1.14674(11) 0.0403(3) Uani 1 1 d . . . . .
H13 H 0.346752 0.781089 1.100376 0.048 Uiso 1 1 calc R U . . .
C14 C 0.25738(17) 0.74970(13) 1.25890(12) 0.0416(3) Uani 1 1 d . . . . .
H14 H 0.296726 0.855301 1.288418 0.05 Uiso 1 1 calc R U . . .
C15 C 0.12005(17) 0.50162(13) 1.28458(11) 0.0383(3) Uani 1 1 d . . . . .
H15 H 0.060448 0.429598 1.332409 0.046 Uiso 1 1 calc R U . . .
C16 C 0.14585(17) 0.44808(13) 1.17359(11) 0.0379(3) Uani 1 1 d . . . . .
H16 H 0.105593 0.341916 1.146183 0.046 Uiso 1 1 calc R 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 6 -1 0.055
5 0 -3 0.0947
3 -6 0 0.0674
0 -6 2 0.0757
-5 0 3 0.0919
0 0 -7 0.0283
5 -1 0 0.0887
0 0 7 0.026
0 4 4 0.0525
-2 -3 -2 0.0761
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 117.32(10) . . ?
N3A N2A C9 112.4(5) . . ?
N2A N3A C12 114.2(4) . . ?
C18 C17 C9 128.1(17) . . ?
C18 C17 H17 116 . . ?
C9 C17 H17 116 . . ?
C12 C18 C17 127.0(16) . . ?
C12 C18 H18 116.5 . . ?
C17 C18 H18 116.5 . . ?
N3B N2B C9 96(5) . . ?
N2B N3B C12 95(5) . . ?
C14 N4 C15 117.43(10) . . ?
O1 C1 C2 121.81(9) . . ?
O1 C1 C6 118.10(10) . . ?
C2 C1 C6 120.09(10) . . ?
C1 C2 C3 120.30(9) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
O2 C3 C2 121.90(9) . . ?
O2 C3 C4 118.17(10) . . ?
C2 C3 C4 119.92(10) . . ?
C5 C4 C3 118.88(11) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C4 C5 C6 121.96(10) . . ?
C4 C5 H5 119 . . ?
C6 C5 H5 119 . . ?
C5 C6 C1 118.82(11) . . ?
C5 C6 H6 120.6 . . ?
C1 C6 H6 120.6 . . ?
N1 C7 C8 123.82(11) . . ?
N1 C7 H7 118.1 . . ?
C8 C7 H7 118.1 . . ?
C7 C8 C9 118.07(10) . . ?
C7 C8 H8 121 . . ?
C9 C8 H8 121 . . ?
C10 C9 C8 118.75(10) . . ?
C10 C9 C17 118.9(9) . . ?
C8 C9 C17 122.2(9) . . ?
C10 C9 N2A 115.9(3) . . ?
C8 C9 N2A 125.3(3) . . ?
C10 C9 N2B 153.9(15) . . ?
C8 C9 N2B 87.3(15) . . ?
C11 C10 C9 118.71(10) . . ?
C11 C10 H10 120.6 . . ?
C9 C10 H10 120.6 . . ?
N1 C11 C10 123.28(10) . . ?
N1 C11 H11 118.4 . . ?
C10 C11 H11 118.4 . . ?
C18 C12 C13 116.4(9) . . ?
C18 C12 C16 125.0(9) . . ?
C13 C12 C16 118.55(10) . . ?
C13 C12 N3A 116.3(2) . . ?
C16 C12 N3A 125.2(2) . . ?
C13 C12 N3B 153.3(14) . . ?
C16 C12 N3B 87.5(14) . . ?
C14 C13 C12 119.00(10) . . ?
C14 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?
N4 C14 C13 123.30(11) . . ?
N4 C14 H14 118.4 . . ?
C13 C14 H14 118.4 . . ?
N4 C15 C16 123.25(10) . . ?
N4 C15 H15 118.4 . . ?
C16 C15 H15 118.4 . . ?
C15 C16 C12 118.46(10) . . ?
C15 C16 H16 120.8 . . ?
C12 C16 H16 120.8 . . ?
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 1.3599(13) . ?
O1 H1 0.84 . ?
O2 C3 1.3581(14) . ?
O2 H2A 0.84 . ?
N1 C11 1.3356(15) . ?
N1 C7 1.3408(15) . ?
N2A N3A 1.246(4) . ?
N2A C9 1.455(5) . ?
N3A C12 1.486(3) . ?
C17 C18 1.323(10) . ?
C17 C9 1.403(18) . ?
C17 H17 0.95 . ?
C18 C12 1.255(9) . ?
C18 H18 0.95 . ?
N2B N3B 1.241(10) . ?
N2B C9 1.56(6) . ?
N3B C12 1.72(6) . ?
N4 C14 1.3365(15) . ?
N4 C15 1.3426(15) . ?
C1 C2 1.3883(15) . ?
C1 C6 1.3937(15) . ?
C2 C3 1.3940(16) . ?
C2 H2 0.95 . ?
C3 C4 1.3943(15) . ?
C4 C5 1.3832(17) . ?
C4 H4 0.95 . ?
C5 C6 1.3857(17) . ?
C5 H5 0.95 . ?
C6 H6 0.95 . ?
C7 C8 1.3795(16) . ?
C7 H7 0.95 . ?
C8 C9 1.3918(16) . ?
C8 H8 0.95 . ?
C9 C10 1.3888(15) . ?
C10 C11 1.3810(16) . ?
C10 H10 0.95 . ?
C11 H11 0.95 . ?
C12 C13 1.3818(16) . ?
C12 C16 1.3936(16) . ?
C13 C14 1.3799(17) . ?
C13 H13 0.95 . ?
C14 H14 0.95 . ?
C15 C16 1.3829(16) . ?
C15 H15 0.95 . ?
C16 H16 0.95 . ?
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 1.92 2.7621(12) 177.3 . yes
O2 H2A N4 0.84 1.94 2.7792(12) 176.8 2_667 yes
